Talk me through my HSA wash sale

[Tom Kazansky]

One small consideration - I believe there's a six month rule if you end up selling VTEB/VTEAX later at a loss:

https://www.whitecoatinve...

[Tom Kazansky]

I believe this is referring to muni bonds such as VTEAX / VTEB...

[Tom Kazansky]

It's easy, but a little annoying in that you can only exchange funds by percentage, and orders need to be placed by noon eastern time....

[Tom Kazansky]

This is something I've been considering regarding auto conversion of a 12/31/21 after tax 401k contribution. Decided to abort the contribution to avoid...

[Tom Kazansky]

Can you direct your retirement contributions toward a money market fund? Then distribute accordingly beyond 30 days?...

[Tom Kazansky]

Dilemma regarding 12/31/21 after-tax contribution:

Can Fidelity be trusted to auto convert the 12/31/21 contribution to Roth before Jan 1st?...

[Tom Kazansky]

Thanks - I do have a small loss in after tax 401k.

Trying to understand what the consequences would be if converted in-plan....

[Tom Kazansky]

What happens if you have a loss on an in plan after-tax roth conversion in a 401K?

For example a $5000 after tax contribution that is converted...

[Tom Kazansky]

Nice post from PoF who went deep on this topic:

https://www.physicianonfire.com/international-stock/

[Tom Kazansky]

This is an interesting point.

Due to an acquisition of my spouse's company that resulted in "short plan year" / excessive 401k...

[Tom Kazansky]

I use VTI, and include the dividends when calculating CA tax (also small amount of interest from the mandatory savings account)

[Tom Kazansky]

Spouse and I have been circling CGMs for a while now. Seems like it could be a very enlightening experiment. Any thoughts on Dexcom G6 vs Freestyle Libre...

[Tom Kazansky]

If you live in CA or NJ, you may owe state taxes on HSA capital gains...

[Tom Kazansky]

Depending on where you live, you may owe some state tax if you sell funds with capital gains in order to do your transfer/rollover....

[Tom Kazansky]

I would consider keeping the Traditional TSP for 2 reasons:

1. The ability to roll future Traditional IRA or 401K money into it.
...

[Tom Kazansky]

The simplest solution would be to increase W-2 withholding....

[Tom Kazansky]

I use the G Fund, but am curious to hear opinions about Vanguard Retirement Savings Trust II / III/ IV which I also have access to....

[Tom Kazansky]

EF is at Ally.

I know the G Fund is popular with many on the forum, but I'm also curious to hear thoughts on stable value funds such as Vanguard...

[Tom Kazansky]

Also on the table...

[Tom Kazansky]

3/9/2020 - sold multiple VTI shares (Cost basis range $144 - $159) in taxable account at a loss.
Sale price - $141

3/18/2020 - created...

[Tom Kazansky]

If you "cashed them out", you may owe some capital gains tax.

Monthly dividends/interest would be fed tax free....

[Tom Kazansky]

Google Sheets with formulas that auto-update for each holding (shares must be manually entered).

Added bonus - great app....

[Tom Kazansky]

Some ESPP experience here:

15% discount, 6 month lookback provision, we usually sell on "purchase day" - it has been a no-bra...

[Tom Kazansky]

With RSUs, they are taxed as ordinary income at the market value at the time of vesting/delivery. There isn't any more tax advantage than if you chose...

[Tom Kazansky]

What I've found most helpful with RSUs has been to ask myself if the amount that vested was in cash instead of stock, would I buy the same amount of company...

[Tom Kazansky]

RSUs?...

[Tom Kazansky]

Thank you, Tangler. Very generous post....

[Tom Kazansky]

Any reason to choose PFF over PFFD?

[Tom Kazansky]

Trekking poles help prevent this....

[Tom Kazansky]

Thread needs a revisit from EntrepreneurMD? Calm the FOMO nerves?

[Tom Kazansky]

State Municipal Money Markets

[Tom Kazansky]

Looks like yields bumped up quite a bit?...

[Tom Kazansky]

Already scheduled auto pay with TurboTax for federal tax due.

Looked into changing this date. Seems you need to call IRS and cancel....

[Tom Kazansky]

Vanguard flags and adjusts automatically in "realized gains and losses" section....

[Tom Kazansky]

Associate dentist here:

Office that I work at is closed for 2-3 weeks except for emergencies, and I will not be paid during this time. ...

[Tom Kazansky]

I get a lot of joy out of Starbucks or other coffee shop gift cards....

[Tom Kazansky]

Thanks again, Hank. So, with recent changes, it does seem possible now to extract only the Roth portion of TSP and rollover to Roth IRA  (I'm no lon...

[Tom Kazansky]

Thanks, Hank. I'm actually interested in the opposite - moving the Roth portion of my old TSP out to my Roth IRA. Sounds like you can't slice and dic...

[Tom Kazansky]

Became interested in this recently - seems there is no way to rollover/transfer ONLY the Roth portion of an old TSP to Roth IRA? Want to keep the TS...

[Tom Kazansky]

I'm considering renting from The Black Tux next time I need to wear one.

Anyone have any experience?

[Tom Kazansky]

A lot of my dentist friends (as well as patients) use and love Slack.

[Tom Kazansky]

Any changes in strategy with TD Ameritrade cutting trading fees?

[Tom Kazansky]

Thanks, Lordosis. Out of curiosity - what did you not like about the Devenir funds? They had Vanguard Target Date funds when I looked recently, as w...

[Tom Kazansky]

Looks like Devenir has 0.30 annual fee.

Leaning toward using TD Ameritrade and investing in SPTM as advised earlier in thread.

[Tom Kazansky]

Catching up with this thread: We're in process of transferring from HealthEquity to HSA Bank due to employer change. It looks like Devenir offers Van...

[Tom Kazansky]

Hey mtbwalt - did you end up lump investing?

[Tom Kazansky]

Can anyone help me interpret this CA rule for the Second quarter? Important: California differs from federal. To avoid an estimate penalty, you must pa...

[Tom Kazansky]

edwinebert wrote: Hey Tom, I know it’s been a couple years but I just came across your post.  I have money tied up in my SEP IRA preventing me from doing the backdo...

[Tom Kazansky]

OP - what did you decide to do?

[Tom Kazansky]

spiritrider - thank you for helping me untangle this. To clarify my general understanding for the 2019 portion: - As long as excess contributions ar...

[Tom Kazansky]

Thank you, everyone, for the helpful feedback. spiritrider - I've been studying the areas you highlighted in Pub. 969 - thank you. This appears to ...

[Tom Kazansky]

Health Insurance Timeline: 2018 - Spouse started new job with HDHP in November 2018, but still had non-HDHP from former employer through Nov. 30th 2018....

[Tom Kazansky]

Another vote for Taos

[Tom Kazansky]

Thank you all for the feedback. In kind transfer sounds like the way to go.  Will look into it. Both IRA funds and new 401K are with Vanguard - fee...

[Tom Kazansky]

We have an opportunity to clean up spouse's IRA situation (SEP and Rollover IRAs) by rolling into spouse's new 401K. The goal would be to enable spou...

[Tom Kazansky]

Thank you, as always, for the feedback. I clicked the "upgrade" button on the Vanguard site under Spouse's Roth IRA account, which appeared to become a...

[Tom Kazansky]

Hi all - TLH'ed Vanguard Total International to VEU in my taxable account late Oct. With Vanguard recently lowering threshold for Admiral shares, I c...

[Tom Kazansky]

Thank you all for the feedback. Is there any disadvantage to using the SEP-IRA --> TSP strategy vs. opening a solo 401K?    ...

[Tom Kazansky]

Got a little 1099 income coming in this year - about 2K, however it could end up being a more meaningful amount in 2019. Been reading up on solo 401...

[Tom Kazansky]

Thank you for the feedback. While we're at it - it looks like we may be able to roll spouse's Vanguard SEP-IRA and Vanguard Rollover IRA (about 200K...

[Tom Kazansky]

Spouse started new job --> new 401K plan administered by Vanguard. Here are a couple of funds under consideration: Vanguard Institutional 500 Index...

[Tom Kazansky]

The 400K-500K required to become an owner is also often glossed over.

[Tom Kazansky]

Spouse had Vanguard Total International dividends reinvested in her Roth and taxable accounts on 9/25/18. I have VXUS in taxable, with a purchase as...

[Tom Kazansky]

Peds and jacovlu - If dividends were received/reinvested for Vanguard Total International Stock on 9/25/18, is it ok to pull the trigger on 10/26/18...

[Tom Kazansky]

I'm getting hung up on some of the wash sale details.  Here's the situation: My taxable: Vanguard Total Intl (VXUS).  Made a purchase Oct 4th Spouse...

[Tom Kazansky]

Me too!

[Tom Kazansky]

Are there any issues with buying shares of the fund you're planning to TLH into leading up to the TLH transaction? (I'm waiting for 30 days to pass since...

[Tom Kazansky]

ahnathan - I think I understand your question because I had the same confusion at one point. What clicked for me was thinking of the backdoor roth as a t...

[Tom Kazansky]

For what it's worth, my wife and I bought her vested shares at her first start up job. We had a 3 month window to buy the shares when she left.  Spe...

[Tom Kazansky]

Thanks, Zaphod - agree that risk tolerance is very difficult to calibrate having not yet had any money during a bear market.

[Tom Kazansky]

Thanks, Peds! We do have retirement account options, including TSP account from previous employment, so I have access to the G and F funds. Sounds like I...

[Tom Kazansky]

Hi - Hope everyone is having a great weekend. Looking for a little advice here: Our investments are almost 100% in stocks. We do have a good sized...

[Tom Kazansky]

Hi, everyone.  Thank you in advance for any advice for our situation. I recently left a full-time dentist position where I was fortunate to have acc...

[Tom Kazansky]

Thank you for the responses!  I'll sleep soundly tonight  

[Tom Kazansky]

Hi All - Did my first Backdoor Roth IRA this past week with Vanguard (thank you, WCI, for tutorial). Followed the steps and converted as soon as the...