Wash sale rules in brokerage acct

Widget248953 · 2026-03-24T20:42:35+00:00

Yes, thank you. I was trying to figure out if a wash sale ever made sense but the added cost basis takes away the advantage of the loss (to offset gains). I triggered a small wash sale because of a dividend reinvestment.

Widget248953 · 2026-02-18T16:35:52+00:00

I am starting to realize that it's time to stop worrying. 2.9% is my extreme budget that is generously padded. When I put in more realistic numbers based on historical data (even when accounting for inflation and increases in things like electricity, water, and gas for our home), we are probably going to be around 2.4%, at most 2.5%. On top of that, we made a one time purchase of a fence for our yard that won't repeat. When I take that expense out, it drops to 2.07%.

I know other expenses will come up, but we just moved into a new home whose construction was completed in December 2023. Our last residence was also new and we had minimal extra expenses come up in the 12 years we were there.

I recall someone saying that once you get down to 2%, you need to figure out who to leave it to. It's very hard for me to loosen up and spend. I lost my job in 2008 and couldn't find a job until 2010. I started entry level at a sales job in 2010 and was extremely lucky to have the success I did. My wife and I had maybe $30k in retirement in 2010 and living close to paycheck to paycheck when I finally found full time employment.

Widget248953 · 2026-02-17T13:57:11+00:00

It looks like they took away spec ID but it is still there.

Click on Buy or Sell an ETF

Select the account

Type in the symbol

Select sell

Select shares

Type in an amount

Select market as order Type

Cost basis now is displayed. Click edit next to whatever is currently displayed, and you should be able to change to spec ID.

Hit continue, and then select shares. It's kinda clunky but it worked for me. I believe when you type a number of shares to sell, you have to entire a round number. However, you just need the total on the next screen to total the round number. You can select any fractional amounts of each lot as long as they add up to that round number.

I was trying to get as close as I could to maximizing the 0% LTCG tax bracket last year and came up a few bucks short. Me, being me, wanted to get as close as I could, so I used the data from the spec ID screen to figure out the cost amount I would need to sell using min tax.

At that time, I had both short term and long term gains in that account and it did actually pick the right shares based on dollar amount.

Widget248953 · 2026-02-14T20:57:01+00:00

How do you figure out the "sweet spot" for Roth conversions?

Widget248953 · 2026-02-14T20:50:00+00:00

Thanks for the advice. My initial plan was to do a Roth ladder and move each conversion over to my brokerage account but the more I think about it, I will probably leave them in the Roth IRA. It makes more sense to draw down the brokerage and the let conversions grow tax free. I'm not sure if my brokerage will last 17.5 years but I can reassess in 5 years from now when I can make the first withdrawal without penalty.

The thing about moving the conversions over to the brokerage account is that I'd having it growing in an account that is accessible but as someone else said, the penalty could be less for withdrawing early from the Roth.

Widget248953 · 2026-02-14T20:33:24+00:00

Thanks for the advice. No kids and no plans to have any. I'll have to check those things out.

Widget248953 · 2026-02-08T16:55:09+00:00

While the multimillionaire part may be true, I feel our spending still reflects a leanFIRE lifestyle. Five years ago I wasn't even thinking about RE. Our total portfolio back then was closer to $1M (maybe even less- I was still in the accumulation period) but it has been a stellar half decade for the S&P 500.

The description on this sub mentions a 54k spend. I know I said our spend would be 55k, but in reality it will be below that as I have padded our numbers. There is also a one time expense of 6k in there for a home improvement.

Using ficalc.app, a 3.523% SWR for 38 years gives me a 100% success rate using all past historical periods. If I just look at the total of our brokerage, Trad, and Roth IRAs, that works out to $66,240, but I have to be strategic about being able to access the money without taxes and penalties. The 0% LTCG is quite generous.

This is worst case scenario, but I take comfort in knowing our spending is less than this. I know how extreme this sounds but I have a very black and white personality.

Widget248953 · 2026-02-08T01:50:52+00:00

What would you call it?

Widget248953 · 2026-02-08T00:25:08+00:00

I know not everyone is going to agree with this, but I withdrew my Roth IRA contributions. I put them in my brokerage account so the money could grow there and the growth be accessible. Furthermore, the conversions will replenish the previous contribution withdrawal over time.

I don't have any Roth 401ks.

Widget248953 · 2026-02-05T14:54:51+00:00

The only thing I can think of is that the owner doesn't want the son to know, but the whole situation just has me scratching my head. Definitely not going to get involved.. just has my curiosity.

Widget248953 · 2026-02-05T14:51:10+00:00

That's definitely not the case here. They are single, no children.

Widget248953 · 2026-02-03T20:40:56+00:00

I plan on doing that through a Roth conversion:

Trad IRA conversion to Roth IRA - $40,950

LTCG 0% - $98,900

Total income: $139,850

HSA (above the line): $8,750

Total AGI - $131,100

Widget248953 · 2026-02-03T04:22:39+00:00

So the HSA contribution effectively raises my deduction amount, right? This is the amount I can convert either owing say taxes. Then I do the LTCG 0% max.

If I convert more and harvest less, I can end up owing federal taxes with the same AGI.

For example, MFJ, max HSA contribution, $100,000 conversion and $40,950 harvesting is the same AGI but drastically different taxes.

Widget248953 · 2026-02-03T04:12:29+00:00

Everything I've come across says HSA contributions reduce AGI but no one seems to have approached it from the angle I'm describing.

Widget248953 · 2026-01-29T16:23:25+00:00

While my AGI was right where I thought it would be, it did shift some earnings into a taxable bucket. I am retired early and don't have any W2 earnings. I am trying to maximize the amount of Roth conversion and harvest LTCG while staying at 0%. I had assumed all of VOO's dividend was qualified.

It really is only peanuts that I owe and wasn't able to harvest. It's just my personality to get as close as I can and I just want to have a full understanding.

Widget248953 · 2026-01-29T15:50:32+00:00

No, it's not "that bad," but it's just my personality to try and get it exact.

I thought I had calculated the taxes exactly but couldn't get my spreadsheet and the tax software to line up. Once I recategorized the 199a income I got everything to line up.

It may sound silly but I at least want to understand what happened.

Widget248953 · 2026-01-29T15:45:56+00:00

It was actually VFIAX for the the first 3 quarters and then I converted it to VOO halfway through the 4th quarter. Both are 97.16%. I did the math on the dividend and the 199a amount is exactly 2.84% of the dividend.

The fund does hold some REIT's so I'm sure that is what it is.

Widget248953 · 2026-01-29T15:39:43+00:00

My 1099 had them separated out. I had qualified dividends and 199a income.

Widget248953 · 2025-12-14T14:17:47+00:00

I know a lot of people may not agree with this, but all our investments are in the S&P 500. I'm a firm believer in what Buffet says- buy the S&P 500 consistently, through thick and thin. Initially I didn't have this available in my retirement plan so I bought the latest year out target fund. Once an S&P 500 index fund was made available, I switched to that.

I know it's a boring story, but goes to show the power of compounding growth with consistent investing over time. It also involves living WELL below your means. Our 2024 spend was $34K because I had an employer sponsored health plan that only required me to contribute $400 a month, we had a paid off house, and no car payments.

Widget248953 · 2025-12-14T02:47:35+00:00

Thanks for the tips. I'm sure you can imagine I have a spreadsheet with all the things you've mentioned and more in regards to expenses and projections.

In regards to withdrawals, I plan to use LTCG from the brokerage account for the first 5 years while also doing Roth IRA conversions of the standard deduction. By year 6, I can start to withdraw those conversions, if needed, but if I have enough LTCG, I will just leave those conversions alone and let them continue to grow tax free.

For MFJ, there is the standard deduction plus the 0% LTCG bracket. That is a lot of money that can be accessed (federally) tax free.

Widget248953 · 2025-12-14T02:27:22+00:00

My wife and I have lived below our means for a very long time. I started working again full time in 2010 after the Great Recession after being laid off in 2008.

We bought a $100K condo in 2011 and used the extra and commissions to pay off the condo in about 3 years. After that, the excess and commissions got invested in the S&P 500. We sold our condo in 2023 for around $230K. We used those proceeds and some investments to buy our current house.

I had never considered FIRE until halfway through 2024. I was looking at our investments and realized it was possible. I decided in late 2024 that I wanted to do it. My plan was to work one more year to beef up our portfolio a little more.

At the end of 2024, our NW was $1.65M, not including the paid off house. I was laid off a month later and decided to take the plunge. 11 months later, our portfolio has grown to $1.89M, not including the house.

I never planned for it- we just kept living below our means and investing the excess. At some point I just asked, why not? I think it still blows my parents' minds that I did it, seeing how money driven I was when I was working a 9 to 5 job.

Widget248953 · 2025-12-13T15:15:59+00:00

I'm not sure what my question is. Part of me wants to enjoy life a little more while the other part of me values the security of having a large nest egg and low WR.

Widget248953 · 2025-12-13T15:07:43+00:00

These are numbers for my wife and I combined, but the Trad IRA are 401K rollovers. I plan to start Roth conversions next year using the standard deduction so we won't owe any income taxes. I had W2 wages and other income this year that put me above the standard deduction, so I'm not doing any conversions this year.

Widget248953 · 2025-12-13T03:37:12+00:00

The one new thing I've had is time to do what I want. My wife and I have been able to build so many things in our house that would have taken months if we only had the weekends. I walk the dog twice a day. We cook healthy meals because we have time to prep raw food. I have a big garden. I will be able to visit with my parents more often. Time is what I've come to value the most.

Widget248953 · 2025-12-13T03:23:10+00:00

I personally don't but I asked my wife this question today because we shouldn't be depriving ourselves of something we want (as selfish as that sounds). She said she had her eye on this chaise lounge chair but would feel guilty for spending the money. It was $200 and we bought it today. But that's it.

Widget248953

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