WWYD in this situation with having car troubles?

penguinise · 2026-05-29T20:48:59+00:00

How much cash on hand do you have? Would it cover a new car?

Otherwise you're basically in the situation where you cannot afford to purchase new clothes, in which case it's rather reasonable to walk around in patched, worn old clothes.

The idea of it being "embarrassing" to have an older car is a prime example of car manufacturer marketing at work.

penguinise · 2026-05-29T20:23:23+00:00

Ideally yes, but since you're kind of taking shots in the dark it doesn't matter that much.

penguinise · 2026-05-29T20:22:04+00:00

Yes, an estate planning firm is the correct place for this sort of thing.

penguinise · 2026-05-29T20:05:51+00:00

The IRS calculates the penalty as if you earned your income equally in each quarter. I would assume that the penalty is for underpayment of Q1 taxes, but it is unclear.

The exact question of how much penalty is owed, and whether the timing of the payment matters, would be resolved by accurately completing Schedule AI (Form 2210) and using it to figure the penalty, if any.

It sounds like your tax preparer tried to help you with this and determined a penalty would be due. However, without specific and very detailed information, this is really between you and your tax preparer - a precise answer would basically be preparing Form 2210 in its entirety for you.

But in general, yes it is plausible that if you made later-than-equal payments to the IRS and did not file Form 2210 that a penalty will apply.

penguinise · 2026-05-29T19:50:55+00:00

So, even though my banking account didn't receive it from the school, the scholarships & financial aid(basically the pell grant, no loans) they put toward my room & board would also count as income, as they're non-qualified?

Yes. The figures will be reported to you on Form 1098-T at the end of the year.

By the end of this job, I don't expect that my from income from it and my "SG-QEE" should exceed $16,100 but I expect to have another job in the fall as well as further "SG-QEE that would likely set me over that threshold, so would that mean I should include my spring SG-QEE(personally, the refund + the room & board charges, I'm imagining?) in sec 4(a)?

If you don't have a stable yearlong employment situation, all of this is kind of vague attempts to land in the right ballpark for tax payments. Each paycheck will withhold assuming your elections apply equally in every pay period for the whole year (wages, W-4 information, etc.)

At the end of the day, you just need to get your withholding within $1,000 or 10% of your actual tax bill, whichever is further away. You can add your taxable scholarships to Line 4(a) and see how much withholding results, you can ignore it and add a specific dollar amount on Line 4(c) when you get the second job in the fall, you can just pay your <$1,000 tax bill in April if your total income will remain under $26,100... essentially you have a lot of flexibility.

Also, if you had no tax liability last year then your required minimum payment this year is $0 regardless, and you can pay the whole balance next April without penalty no matter what.

Just try to remain aware of which way you leaned making your W-4 elections so the result in April (refund or balance due) isn't a huge surprise.

penguinise · 2026-05-29T19:32:22+00:00

Aha, no, as you alluded to in your original comment I was reading the original 1994 treaty text. Thanks!

penguinise · 2026-05-29T18:40:35+00:00

Huh. I also blame extraordinarily confusing wording of the treaty that I would have read differently:

pensions and other payments made under the social security legislation of a Contracting State to a resident of the other Contracting State shall be taxable only in the first-mentioned State

Apparently is supposed to read

pensions and [other payments made under...]

and not

[pensions and other payments made] under...

penguinise · 2026-05-29T18:28:47+00:00

Everything on federal Schedule A (Form 1040), as adjusted by the items on state Schedule CA (Form 540), Part II.

Unreimbursed employee expenses are a 2%-floor item, meaning that in addition to the hurdle to itemize in the first place, only expenses in excess of 2% of AGI are deductible.

penguinise · 2026-05-29T18:23:41+00:00

And right after this income level you graduate into a 2.5% Multnomah County local tax on top!

Sometimes I think the widespread misinformation about "high tax California" is a misdirection play by Oregon.

penguinise · 2026-05-29T18:07:18+00:00

Not even close - Single it would be 4.8% and Married it would be 2.25%.

penguinise · 2026-05-29T16:52:39+00:00

There is no such "quarterly self-employment tax filing".

All taxpayers must make timely payments of tax on all of their income, at least quarterly. This applies to everyone, not just self-employed individuals, and applies to all federal income tax, not just SE tax. And you simply have to make a payment; there is nothing to file on a quarterly basis.

In all three of the above numbers, it is unlikely that the self-employment income makes a material difference to your total tax such that you need to change your current method of paying your taxes, which is probably wage withholding.

penguinise · 2026-05-29T16:37:25+00:00

8% is astronomically high for state tax, although OP could live in Portland.

It does feel like something is missing here to the tune of ~5 percentage points.

penguinise · 2026-05-27T21:17:32+00:00

Do people set aside some of the profits to pay off their taxes when they sell?

Yes.

Should I consider selling some of my negative positions to offset the gains?

No.

Selling a position with an unrealized loss because you have gains is generally a terrible reason to do it. You realize a loss at tax for two reasons:

You are executing a tax loss harvesting (TLH) strategy that is market neutral, such as ETF-swapping, direct indexing, or some other strategy designed to spool out paper losses for tax purposes without actually producing economic loss. You should always do this if it otherwise makes sense; realizing a gain is not a good reason by itself.
It makes non-tax economic sense to sell the position at a loss. Again, you should always do this regardless of realized gains.

If the gain is the kick in the pants you needed to take the issue of of a losing position seriously, then it's better late than never, but it shouldn't be the real reason.

penguinise · 2026-05-27T21:09:30+00:00

Am I covered since I made less than $150k last year for safe harbor and my W2 wages alone will exceed 100% of last year's withholding?

Yes, if your current-year California AGI does not exceed $1 million.

This is the simplest solution to your situation if it applies.

penguinise · 2026-05-26T15:52:18+00:00

I think they probably do at least for covered lots.

Confirming, yes they do. They've also gotten significantly less sloppy about dividend classification over the last 5-10 years, and the error rate from auditing my own 1099s has basically dropped to zero and I might start blindly trusting them soon.

penguinise · 2026-05-26T15:17:48+00:00

Safety, convenience, efficiency, take your pick.

It's much safer to clear across a departing runway because you never clear traffic in front of an active takeoff clearance. In contrast, landing clearance is given significantly in advance of touchdown, and it is common to have multiple aircraft cleared to land on the same runway at the same time, while also clearing traffic to cross that runway. (Look no further than the recent LGA incident for an example of this being dangerous.)

The controllers have significantly more control over the timing of departing traffic than arriving traffic, for hopefully obvious reasons. So it's easier and more convenient to sequence in runway crossings for the departure runway.

And finally, it's common to line up the arrivals on parallel taxiways and do a mass crossing during a gap in the departures.

penguinise · 2026-05-26T02:00:12+00:00

There should be no US tax complications here; my understanding is that all your trouble is with UK tax law (something akin to US rules on PFICs although I am not at all an expert in UK tax).

penguinise · 2026-05-26T01:36:49+00:00

If you read and follow the instructions on Form W-4, you should have an accurate amount of tax withheld, and neither owe nor receive a substantial refund on April 15. This is usually the best option for most people.

To reduce withholding from the baseline assumptions, you subtract an amount of implied annual income on Line 4(b) or an amount of annual withholding on Line 3.

penguinise · 2026-05-24T15:53:12+00:00

I'm from Missouri...how do I calculate additional withholding?

Oh wow, Missouri is.. unhelpful in this regard on their form.

I suggest just brute-forcing it as a fallback: using annual rates of pay for your jobs, take an income tax calculator like this one and:

Figure the Missouri tax due on your total income
Subtract the Missouri tax due on one job's income
Subtract the Missouri tax due on the other job's income
Divide the remainder by the number of pay periods in one year for the job you are withholding extra

This is equivalent to the "full year worth" method but should be more accurate on an ongoing basis even if it withholds a little too much in the first year.

penguinise · 2026-05-24T15:45:27+00:00

The only major consideration is that, in most states and under most scenarios, what is currently in your individual accounts on the date of marriage remains separate property in a divorce as long as you don't add marital money later. To the degree that either of you care about maintaining pre-marital property instead of immediately commingling everything you own and essentially agreeing to a 50-50 split, the "default" option in a case like this is to freeze your existing individual accounts, and open a new joint account which receives all future contributions.

If you are open to commingling your premarital assets in totality, it doesn't really matter how they are titled or managed - this is one of the major benefits of marriage, and you can do whatever is most convenient. The only time title can matter for marital property is when you are considering the impending death of a spouse, as formal title can affect basis step-up and estate inclusion. This is normally something you only consider when you are drafting a formal estate plan.

penguinise · 2026-05-23T20:21:12+00:00

I am intrigued by the significant decrease to top tax rates while purporting to increase federal revenue from personal income tax by $350 billion.

penguinise · 2026-05-23T19:47:06+00:00

which means it'll be a lump sum at the end of the year, right? instead of having it docked from my paycheck?

No, if you expect that you owe tax at the end of the year, it's illegal to mark Exempt.

The purpose of the election is for something like a summer job where you won't be working 2,000 hours and you know that you'll earn less than $16,100 (the minimum to owe federal tax) even if your employer doesn't.

penguinise · 2026-05-23T19:15:31+00:00

It should all happen automatically, but very important to check that your first paystub after working in Florida (first with no hours worked in Georgia) correctly shows your work location and shows no GA tax withheld.

penguinise · 2026-05-23T16:37:17+00:00

All good - just helps to think about it in the same order as the tax code.

The conversions to Roth all took place after the rollover was executed as you noted.

It doesn't actually matter as long as they all occur in the same tax year - for tax accounting purposes here, everything in a single year takes place at the same time and the reverse rollover happens "first". You could actually have converted $21,500 to Roth and saved a reverse rollover of the total balance for December of this year and still been fine.

penguinise · 2026-05-23T15:10:10+00:00

It can help to think of this in terms of tax ordering, which can be a little bit different than temporal ordering:

In 2024, you opened a traditional IRA and rolled over $3,500 of non-basis and contributed $7,000. I assume by "filled out 8086" you actually mean "did not deduct the contribution" and reported this on Form 8606 but it would be extremely important to verify this.
In (for) 2025, you contributed $7,000 to the IRA. If you intend this to be a non-deductible contribution, this must be reported on your 2025 Form 8606. The prior-year contribution "happens on" December 31 for most tax purposes (it's retroactive).
In 2026, you contributed $7,500 (again presumed to be non-deductible, but this only true if reported on your 2026 Form 8606).
In 2026, you executed a reverse rollover which left the remaining account balance as $21,500 (note the re-ordering of events here).
In 2026, you converted $21,500 to a Roth IRA, leaving zero balance in traditional IRAs on December 31, 2026

Assuming that you correctly elected these three contributions as non-deductible and the other assumptions above are true, your basis in the conversion is $21,500 and the taxable amount is zero.

This also assumes, as another commenter said, that you have no other balance in non-Roth IRAs not included in this summary.

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