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Thanks, aja8888 and SecondCor521! You give me hope that this might eventually work out OK. But maybe I'll try to get a reality check from a tax attorney, just to know if I'm as much in the right as I think I am.

Yes, essentially. "On time" for the 2020 return is October 15, 2021 (if you filed a time extension), but you are still entitled to your refund if you file by 3 years after that, i.e. October 15, 2024. I filed my 2020, 2021, and 2022 returns a couple of months ago, trying to get caught up. No...

Yeah. It's too late for me to follow this advice, unfortunately. I have to do battle now, if I don't want to pay penalties and interest for 2020 despite being ALWAYS overpaid at the IRS.

You have the right idea conceptually, though I stopped doing this after my 2019 Form 1040 and asked for a refund on my 2020 Form 1040. My big problem is that after they send me refund checks for 2017 or 2018 or 2019, I appear to owe them taxes, penalties and interest for 2020! Grrr.

I'm pretty sure these are real government checks. The IRS has acknowledged my return of some of them without any mention that they were scams.

Can anyone guess why the IRS keeps issuing refund checks for tax years where I asked for the refund to be applied to the next year? It seems to have started with my 2017 return. Is it relevant that I don’t pay estimated taxes? In other words, is this option to roll your refund forward only...

Having myself received a few IRS letters, I strongly recommend you read the letter carefully to see what THE LETTER SAYS you should do if you disagree with the letter's conclusions. If the letter says you can ignore it, then ignore away. If it says you have a deadline to respond, then respond...

Can you clarify what you mean by "eventually" in your second paragraph? If you expect your window of opportunity to close in 2026 when your partner starts the age-70 SS benefits, and you don't already have LTCGs, then this should be more of a "if it happens, great" thing than a plan per se...

FWIW, there's just no point in obsessing about when you "should" start feeling better. There's no rhyme or reason about who gets what kind of case of COVID-19. I’m sure it’s frustrating to watch your hard-earned physical conditioning go out the window. But one of the consistent lessons...

To the OP: I just ran FIRECalc to explore optimal asset allocations for a 14-year retirement with a $1.1 million starting portfolio and $80k annual withdrawals, and the odds of success maxed out at 82% (with 75% to 85% stocks). With your current 47% stock allocation the success rate was a bit...

This sounds like good advice to me!

One thing you could do for a while, especially if you have significant unrealized capital gains in your taxable (non retirement) accounts, is to take advantage of the 0% tax on capital gains and qualified dividends for taxpayers whose total taxable income is below a certain threshold, which for...

The conventional wisdom says you need a decent amount of stock, not necessarily 80 or 90 percent. What I have found from playing around with FIRECalc is what I'll call the Suze Orman effect. Suze Orman apparently doesn't follow her own advice to others, and holds little or no stock. Sounds...

Read up on ulcers. They are not caused by stress. https://www.niddk.nih.gov/health-information/digestive-diseases/peptic-ulcers-stomach-ulcers/symptoms-causes Your wife might feel better because she followed her doctor's advice, either to take a course of antibiotics or to quit taking too...

Have you tried using the FIRE Calc Investigate option (under the tab labeled "Investigate", which is the rightmost tab at the top of the calculator page) to investigate changing your allocation? It will graph your chances of success (portfolio staying above zero value for the length of time you...

Your expenses all sound fairly immediate, so a slightly conservative but reasonably accurate way to model them is to reduce your starting portfolio by those amounts. Such advisors do exist, but I think there aren't many. Someone I knew did that for a while but didn't stick with it. He said...

Yes. Also due to likely tax hikes in the future, IMHO. Current tax brackets are at all-time lows while budget deficits and the national debt are at all-time highs. I think this country is on an unsustainable trajectory and something will have to give.

One thing I didn't see anyone else mention here: it's a good idea to keep your IRA balance at any one brokerage below the $500k SIPC limit. Sure, it's hard to imagine one of the giants going bust, but you never know. Another random piece of advice: if you have very big balances in non-Roth...

Ha, ha, you do sound frustrated. But I strongly recommend you LISTEN TO THE ADVICE HERE, not to pay a financial advisor at all. They are not worth one thin dime, IMHO, unless you are the excitable type who needs to be talked down from panicking and selling everything after a stock-market crash...

You can manage your own investments with very little effort if you put your money in index funds. We have never paid a financial advisor in any way (neither AUM nor flat fee), nor have we spent more than a VERY minimal amount of time choosing investments, ever. Yet our investment accounts have...

My most-magical list: Crater Lake - weird and gorgeous scenery, the chance to hike up and into a cinder cone (after a short boat ride), VERY cute chipmunks... Mt. Rainier - gorgeous scenery and excellent hikes. Grove of the Patriarchs trail to see and learn about the iconic Pacific Northwest...

But your Roth balance ends up lower than it could have been, so the future earnings will be less than they could have been. The time when you will notice the difference is not now, it's when you start withdrawing from your Roth IRA(s) years or even decades from now. If you pay the IRS from a...

What you do is take a distribution from a tIRA, requesting that a certain amount (as much as you need, but obviously not more than the full distribution amount or 99% of the distribution amount if that's the rule at your custodial firm) be withheld for taxes and the rest be sent to you in some...

Every penny of a Roth conversion is taxable income in the year you withdraw the funds from your tIRA. That's true no matter the details of how you pay the taxes. What some here have pointed out is that you could do a Roth conversion early in the year, sending all the funds from the tIRA to the...

I didn't know this, thanks! Of course first you'd have to decide if a Roth conversion makes sense that year, but if it does then you could also piggyback on it to have tax withheld for other income as well as the conversion itself. You'd just have to be sure to have enough after-tax cash ready...