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Old 02-19-2011, 10:49 AM   #41
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Originally Posted by Aiming_4_55 View Post
I believe Cook County sales tax is about 10.25% for what it's worth. Might of changed since I moved away.
You must be referring to the sales tax in downtown Chicago, not just Cook County. Cook County adds only 1.25% to this total. But the current rate appears to be 9.75% after they got rid of the past Crook County President Todd Stroger and rolled back .5% of his last increase. He added relatives and cousins as the only "qualified" people in the country to do the jobs he hired them for at salaries 2x-3x what they used to make, more if you count the prison pay some of them used to get!
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Old 02-19-2011, 10:55 AM   #42
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Yup, my experience was mainly downtown Chicago.

Sign me up for a ghost job... I'm not lazy, sign me up for 2.

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You must be referring to the sales tax in downtown Chicago, not just Cook County. Cook County adds only 1.25% to this total. But the current rate appears to be 9.75% after they got rid of the past Crook County President Todd Stroger and rolled back .5% of his last increase. He added relatives and cousins as the only "qualified" people in the country to do the jobs he hired them for at salaries 2x-3x what they used to make, more if you count the prison pay some of them used to get!
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Old 02-19-2011, 11:14 AM   #43
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It seems to me that Illinois needs a complete revamp of its tax code. That state is in a world of hurt, and even a 5% (flat) tax rate is extremely unrealistic, given the hole that's been self-dug for the past couple of decades.
From what I read about this, we could make it at 5% (our current rate is 3%) and back down to 3.75% later if our governor would make some serious efforts to pay down debt and cut back spending. Problem is his new budget made little effort to pay down current debt and included a lot of new spending. This is the same guy who got elected on the promise of balancing the budget and being fiscally responsible.
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Old 02-19-2011, 11:15 AM   #44
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Back to income taxes...once off salary most of your income would come from dividends and cap gains, right? That would be 15% federal, subject to change, and until you start getting that pension.
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Old 02-19-2011, 11:25 AM   #45
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Definitely recommend you get some professional help---with a portfolio the size you have you should be able to get a very low percentage price to balance and plan so that indeed you can get most of your money away from the tax collector by doing dividends and capital gains and growing in tax deferred accounts.
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Old 02-19-2011, 11:26 AM   #46
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I mentioned before...once retired I will sell current house and move back to city place so that should reduce my re exposure by 1.7 million. And I love all of my other re and am willing to work another 2 years to make sure I can afford to love it. As far as what I do...I worked on wall street for 8 years doing investment banking...providing mergers and acquisitions advice and have spent the last 9 years running strategy and m and a for a somewhat well known industrial company.

OK, so that gives you a 13.7MM portfolio (9MM stocks, 3MM munis, 1.7MM RE sales proceeds), and if your tax rate averages, let's say, 30% with most of the tax coming from lower LTCG rates (plus your state income tax rate). So you need about 342K/13.7MM, or about a 2.5% SWR rate, which still looks doable to me. Although, I would resturcture that portfolio some so it is not so top heavy with stocks but with more cash reserves. Maybe 10 years of cash reserves so you can make it through "bad times" in the market?

Plus, with your skills, I bet you could do some consulting on the side PT (setting your own hours so it does not seem like a real job), which would lower the SWR and make the projection even more viable.

Dude, you're set! What do you want to do when you quit? Chase mamma around the house all day?
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Old 02-19-2011, 02:12 PM   #47
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I have $6million in stocks and 3 million in laddered munis (not $9 milllion plus the $3million sorry if i confused you on how i wrote that)...if i work another couple of years...i should have another $1.5 to $2.5 depending on how things go. so in 2 years i will have 8 ish in stock and 3 ish in bonds plus the $1.7 ish in RE proceeds from house sale. good advice on getting some professional help...so far ive been doing my own selections.

as far as what i will do...will definitely spend more time with my kids as my current job isn't that difficult...but the travel is absolutely killer. anyway - ill probably end up working with some buddies at a small m and a boutique a couple of days a week...and otherwise be a house husband. maybe my wife will decide to re-start her career (she was a TV newslady). who knows really what i will end up doing..just not doing this and this city!
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Old 02-21-2011, 05:47 AM   #48
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I have $6million in stocks and 3 million in laddered munis (not $9 milllion plus the $3million sorry if i confused you on how i wrote that)...if i work another couple of years...i should have another $1.5 to $2.5 depending on how things go. so in 2 years i will have 8 ish in stock and 3 ish in bonds plus the $1.7 ish in RE proceeds from house sale. good advice on getting some professional help...so far ive been doing my own selections.

as far as what i will do...will definitely spend more time with my kids as my current job isn't that difficult...but the travel is absolutely killer. anyway - ill probably end up working with some buddies at a small m and a boutique a couple of days a week...and otherwise be a house husband. maybe my wife will decide to re-start her career (she was a TV newslady). who knows really what i will end up doing..just not doing this and this city!
Oh, OK. Sorry about that confusion. That still puts you around a 3% SWR. For a super long term ER I would personally want to be around a 2-2.5% SWR. However, if your wife wants to go back to work as a news lady I bet she could kick in some percentage of her salary for the budget to get you back in the 2% range.

IMO you still probably have enough to pull it off, and with your skills you could always go back to work if you had to at some point. I would give it a try while you are still young..............
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Old 02-21-2011, 08:18 PM   #49
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Thx. I think I will work 1 year and 10 months more and then call it a day. Just to make sure I have enough. Thx everyone for their feedback. I feel like I'm very close!!!
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Old 02-27-2011, 12:46 AM   #50
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I'm 40. I have 2 houses worth 2.5 to 3 million. Plus 2 condos worth over a million. And a couple of fractionals 400 ish. I have 9 million in securities...3 million in laddered munis and the rest in diversified equities. I have a pension at 62 of a lump sum of a couple of million. 2 young kids. I estimate retirement expenses of 240 ish. I have no debt. My questions are can I retire? If so what kind of portfolio would you suggest? If I do retire I cant be wrong...I want to avoid having to go back to work at target when I'm 68! So I would need a pretty conservative portfolio. Thoughts?
Goblue1972...A.K.A Charlie Sheen?
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Old 02-27-2011, 03:10 PM   #51
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I wish....
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Old 02-27-2011, 07:05 PM   #52
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The fixed costs are large with the real estate...property taxes 65k, and associated utilities and assessments are another 30 ish. Kids, private school tuition...you get to north of 200 quickly. We love all of our real estate would rather work another year or two than have to sell it.

There is your answer. Just keep working. You would not be as happy without the real estate. You will know when you are ready - you'll either have more money, or you will be more willing to shed some of your expenses.
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Old 02-28-2011, 12:27 AM   #53
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Why would someone with this much money ask questions here? 99.9% of us would never see this in our lifetimes.

Posters who know nothing at all about this economic level nevertheless pitch in to help out. Does anyone think that they would be asking questions of the $400/mo food budget and dryer sheet brigade if they had $10mm?

I know I would not.

Ha
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Old 02-28-2011, 06:15 AM   #54
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Why would someone with this much money ask questions here? 99.9% of us would never see this in our lifetimes.


Ha
I agree. His stated profession is M & A. Surely he has done more complex math calculations when helping people on wall street decide whether to go forward with a merger. Unless they just decide when they get that warm fuzzy feeling, then it is a go. Makes you wonder.
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Old 02-28-2011, 03:36 PM   #55
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I agree. His stated profession is M & A. Surely he has done more complex math calculations when helping people on wall street decide whether to go forward with a merger. Unless they just decide when they get that warm fuzzy feeling, then it is a go. Makes you wonder.
Sometimes it's easier to make decisions when it's other people's money. In m&a, the money belongs to a big corporate somewhere, and it is easier to make the decisions based on the math, and the cold hard facts. But it becomes a little more emotional when it's your own money. This s also why it's sometimes easier for us on this forum to offer advice than it is to even take that advice ourselves. I know that if I followed advice I have given here before, I would be FIREd already (not at 8 digits yet like the OP, but we would definitely survive without eating cat food).

FWIW...

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Old 03-02-2011, 09:31 PM   #56
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Fifty years is a long time for retirement to live on a fixed number. And given my fixed costs already described...I thought it would be beneficial to get some others views on the subject. Yes...I have been doing m and a for 17 years and yes valuation work is a key skill set...however rarely are we asked to look at 50 year scenarios with all of the personal and other variables that could develop over such a long time frame. In addition most of my work revolves around going around the world and romancing targets, due diligencing those targets, negotiating price, and ultimately leading the negotiating of the stock purchase agreement. While these are clearly related skills that give me comfort to manage my own portfolio, it doesn't necessarily prepare me to make these types of personal financial decisions that will impact my family and the sustainability of our lifestyle over such a long period of time.
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Old 03-16-2011, 12:37 AM   #57
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I'm having a hard time believing that you aren't using an advisor? People responding with stuff like "Stick half in munis, half in diversified equities" are being ridiculous. It is especially worthwhile to have a very specifically allocated portfolio, not some general "lazy portfolio" type of thing.

I have about half your money and putting extreme amounts of research into handling it. All roads lead to an affordable advisor. And I've read 40+ books now on finance.

If you haven't already, go join bogleheads. Its a better financial forum IMHO, but I use both sites. There are some good podcasts out there too, and good books to be read.
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Old 03-16-2011, 12:41 AM   #58
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Why would someone with this much money ask questions here? 99.9% of us would never see this in our lifetimes.

Posters who know nothing at all about this economic level nevertheless pitch in to help out. Does anyone think that they would be asking questions of the $400/mo food budget and dryer sheet brigade if they had $10mm?

I know I would not.

Ha

Yeah I'm definitely skeptical. I think someone who has been accumulating this kind of money over so many decades would undoubtedly bump into some better sources of advice. Especially if his business is M&A.
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Old 03-18-2011, 08:29 PM   #59
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I guess I need to send over a w2 Whatever....the money managers I have met tend to be bozos. I feel more comfortable managing my money myself, as I know where every nickel is. There is a guy that has looked at what I have done and has made some helpful suggestions...but fundamentally I'm reluctant to give up control. Don't know how to address your skepticism...but this is really not the purpose of my reaching out to this cite to get some reactions. But if there is a simple way to address your skepticism....let me know.
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Old 03-18-2011, 08:45 PM   #60
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I guess I need to send over a w2 Whatever....the money managers I have met tend to be bozos. I feel more comfortable managing my money myself, as I know where every nickel is. There is a guy that has looked at what I have done and has made some helpful suggestions...but fundamentally I'm reluctant to give up control. Don't know how to address your skepticism...but this is really not the purpose of my reaching out to this cite to get some reactions. But if there is a simple way to address your skepticism....let me know.
"Cite"? Really man?

No one asked for a W2, I think myself and others were just dumbfounded that someone with over 10mm in assets wouldn't have a solid education in all of this. Congratulations for getting to where you are in life.
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