I have a plan, its better then the no plan I had before. Thoughts.

[Slim11]

Since those individual stocks have appreciated highly, they likely will NEVER show losses that can be harvested.

Most likely candidates for TLHing are stocks or ETFs that you've bought in the past six months.
Many retirees are drawing down their portfolio, not investing more in their taxable account, so they will likely not have any TLH opportunities.

Note: an individual stock can go down close to zero in value as the company goes out of business. But an index fund of almost any type will likely never see this happen...

Right, this is why I transfered a small amount of it to the managed account, 20k, have them deal with it, and take 20k out of that managed account buy the end of the year and buy a fund. I tried to figure this out myself, but nothing I buy has any significant looses. And I have a hard time parting with these stocks, semi sentimental I guess. Good thing is I dont add, or only add more to the managed account. Thats maybe 1/4 or less then my total liquid worth.

 

[Slim11]

Sometimes the KISS principle is the way to go. Your plan will keep you busy with many contingencies.

And make me do double takes along the way. Lol. I think If I have a plan, and think about the accounts as seprate, I will help me achieve what I dont have. I know that makes no sense, but I hold the wrong stocks in the wrong accounts because the money is avaliable in them. If I have a few more boundaries I will not do stupid things. We'll not as often anyways. I have been better buying things, I dont sink a ton into one stock now, I split it up amoung a few stocks .

 

[TheWizard]

Right, this is why I transfered a small amount of it to the managed account, 20k, have them deal with it, and take 20k out of that managed account buy the end of the year and buy a fund. I tried to figure this out myself, but nothing I buy has any significant looses. And I have a hard time parting with these stocks, semi sentimental I guess. Good thing is I dont add, or only add more to the managed account. Thats maybe 1/4 or less then my total liquid worth.

At age 76, I add thousands of dollars to my taxable account each year. I might be a bit unusual, but a good general rule in this situation is: never buy anything you aren't willing to hold forever (in your taxable account).

Why?
Because if I'm going to buy a new F-150 (mine is ten years old), then I could either withdraw $70k from Roth or from taxable, or a combination.
If I withdraw from taxable, I'm going to choose the lots with losses or with least gains. The lots I bought more than two years ago will likely never be sold (by me) and will get stepped up basis at some point.

With that in mind, I would just leave those three individual utility stocks alone, but not reinvest any dividends...

 

[Slim11]

I stoped the drips last year, didn't even realize how much they were. Lol. When I was working, I didnt pay that much attention to things. And I will keep at least half of them if not more. Plus some of the other stuff I like and bought small amounts of. These I will keep or sell without much thought. Easier for me to grasp it when its a small amount. My other big holdings are voo, and some cruise stocks. Obviously they are way up and not worth selling. Haven't owned them as long, but I bought a lot of it during covid. Not selling voo. The kid will get a good windfall then.

 

[Texas Proud]

Slim, you are not getting it... Fidelity and Schwab have FREE FAs... and most of them seem to be good...

Why pay for something you can get free... and if you get hit by a bus they will do the same thing that a fee person will do.... OR, whoever does your finances can hire a fee FA...

Why pay for one until then?

 

[walktalk]

Not a bad plan at all, just don’t underestimate how annoying juggling all those pieces gets over time - boring + simple usually wins in the long run.

 

[Kings over Queens]

And make me do double takes along the way. Lol. I think If I have a plan, and think about the accounts as seprate, I will help me achieve what I dont have. I know that makes no sense, but I hold the wrong stocks in the wrong accounts because the money is avaliable in them. If I have a few more boundaries I will not do stupid things. We'll not as often anyways. I have been better buying things, I dont sink a ton into one stock now, I split it up amoung a few stocks .

I've read this thread 3 or 4 times trying to understand your goals, and it seems to me you are doing the opposite of what you intend.

You stated you want to reduce taxes yet you are doing roth conversions at a high tax rate.

You state that your dividends are throwing off too much income and you are selling stocks that create income (and tax).

You are worried about doing stupid things? What stupid things are those? You were also critical of having/holding stocks that were profitable. Most people would wrap their arms around that situation.

I'm a big fan of plans, and I don't mean to be critical of yours, but you asked for thoughts. It seems to me you are creating a lot of financial engineering for the sake of it. I agree with others where keeping it simple can be the best course of action.

 

[TheWizard]

There are different reasons for doing Roth conversions. The simple tax arbitrage reason is only the most obvious.

Some folks Roth convert when MFJ because the eventual survivor will certainly be in a higher tax bracket. This is fine and a form of tax arbitrage.

In my case, Single, I do smallish Roth conversions in the 24% Federal tax bracket to build a Roth IRA slush fund for infrequent large expenses. I expect to remain in the 24% marginal bracket indefinitely under current law, but I could get into the 32% bracket if I'm not careful. QCDs help.

Having said that, my Roth IRA is over $500K now, so likely self perpetuating in my situation. So I could stop doing annual $15,000 Roth conversions going forward. I'm thinking about it...

 

[SnowballCamper]

My pension is 120k, no ss, and I just realized last year cds and dividands, with a small inherated ira is putting me way op on thr earnings chart. Also the rollovers dont help. But if the stuff keeps making money in the retirement plans the distrabutions in 20 years may be worse. And TBH I dont think I need the roth money, but it would be nice to leave for the kido.

It seems like your plan has been to reduce taxes by holding no volatility interest generating assets that barely get you over inflation.
A much better option seems to me to hold assets with primarily capital gains (and not interest). Then you decide how much income you have when you decide to sell them for your expenses. Capital gains taxes are generally less, because you already have income at the 120k level.

 

[Koolau]

It's odd that a FA would tout tax loss harvesting. If I ws hiring a FA I would want a FA that doesn't make picks that lose money.

Yeah, I might even hire someone that can to that!! Does any FA advertise that ability?

 

[Koolau]

Two more things:

Have you run FIRECalc?

FIRECalc: A different kind of retirement calculator

www.firecalc.com

What are you going to do about health care?

 

[Slim11]

Two more things:

Have you run FIRECalc?

FIRECalc: A different kind of retirement calculator

www.firecalc.com

What are you going to do about health care?

I have , I am fine. I get Healthcare from the state at a big cost, but its managble. 1300 now a month. I may downgrade the plan next year. 120k a year pension before taxes helps. The savings are for everything else.

 

[Koolau]

I have , I am fine. I get Healthcare from the state at a big cost, but its managble. 1300 now a month. I may downgrade the plan next year. 120k a year pension before taxes helps. The savings are for everything else.

It really sounds like you are golden then. Glad it's w*rking for you!

 

[Retired Expat]

I just hate managed accounts as that is a big drag on returns...

Plus... you can tax loss harvest IF you actually have losses to harvest...

I did very well with my managed accounts but more importantly than that my FA’s were an invaluable source of referrals to attorneys and other prefessionals and advice that saved me 10x what I paid them in fees.

 

[Koolau]

I did very well with my managed accounts but more importantly than that my FA’s were an invaluable source of referrals to attorneys and other prefessionals and advice that saved me 10x what I paid them in fees.

Now THERE's an advantage I hadn't considered.

I used to count on my CPA for such things when I lived on the mainland. My CPA here seems less "useful" for such things. Thanks for the input.

 

[Slim11]

For me, I get it the fee sucks. And is .75 of a percent. But it isnt on all my things. And they have been outperforming my choices, plus they save on the taxes. Once I get some things moved around, I will slowly withdrawal from that account if I am confident doing so.