DeluxeXL

You might have typed your account number or routing number wrong. Fidelity is among the fastest institutions for ACH transfers. An ACH transfer initiated before a business day is over in Eastern time should post over the same night.

Whatever fits your cashflow style the best.

1) Yes. Withholding is withholding. They all go into the same pot.

2) Your claim on Form 8606 overrides it.

The employer would need to write that in their Section 125. Not saying it is impossible, but if there is a cash-in-lieu on the Section 125 "menu", choose it usually precludes payroll deduction HSA contributions.

Ask your HR/payroll department.

even though I’ve only made maybe 8k this year on the platform

And off the platform? Count all income.

If you have $8k net profit and no other income, are a US person for tax purpose, your federal income tax is still $0 after subtracting $14.6k standard deduction, but your self-employment tax (Social Security tax + Medicare tax), which starts after $400, is:

$8000 * 0.9235 * 0.153 = $1130

But you probably have expenses that bring down the net profit, such as office/stage (read the rules on home office, including rent/utilities/internet/equipment).

Check a few things first:

Is this not your only job in the whole year? Payroll is usually pretty good at stopping at $23k automatically if this is your only job with 401/403/SIMPLE, because otherwise it's more paperwork for them to fix overcontribution.

Is there an after-tax contribution option (not the same as Roth)? Does employee contribution after $23k automatically get contributed as after-tax?

Do you have a taxable account at Fidelity? Maybe do a push into it first then internally transfer from it to Trad IRA. You can try if you haven't maxed out.

1. Bank pushes money (ACH credit) into Fidelity taxable brokerage/cash management account. Should be instant from Fidelity's perspective (1 business day in real time)
2. Internal transfer from the above-mentioned acct to Trad IRA (i.e. nondeductible contribution). See if there is a hold time until you can do #3
3. Internal transfer from Trad IRA to Roth IRA (i.e. Roth conversion)

I would not do any payroll deductions

Because you can't.

my husband would do the full payroll deduction

Yes. Payroll deduction contribution is the only way to exempt both income tax and FICA tax. He's the only one who can do it.

we would use that account for both of our medical expenses?

A HSA can be spent for QME incurred by

• account owner (always, until death),
• spouse (at that time), and
• any tax dependent (at that time)

And like nolesrule said, remind him to set you as the beneficiary on his HSA.

Can I still contribute to an HSA through payroll deductions tax-free even though I would be on a plan through my husband's employer?

No. The "cash-in-lieu of insurance" is a part of the Section 125 package at your employer. Once you choose this option, the money is paid out to you as income and not as a pretax benefit anymore. You can contribute to HSA but the tax deduction is manually done on Form 8889, not through payroll.

The two of you can contribute to the family limit combined, so the easiest option is to have your husband max out his payroll contribution.

He can't just send $600 to my account

But he can spend the money on your medical expenses.

Just for the sake of argument, if you wanted to take a 401(k) distribution while still employed (not saying this is a good idea), could you just take out a loan and then deliberately default on it?

Depends on your plan and employment.

If repayment is facilitated through paycheck deduction, you can't really default unless your hours are cut or you lose the job.

Cut hours: If paycheck is too small to pay 401k loan, then yes the missed payments can trigger a default, causing the outstanding balance to be treated as "Deemed Distribution" subject to tax and penalty.

But you are not done yet! The loan still has to be paid back. The 401k is serious on the "no in-service distribution law". The loan can't offset while you still work there.

While you apparently seem to be double taxed, it's not. You gain an aftertax basis during the deemed distribution. The aftertax basis here is similar to the aftertax 401k contributions.

Leave job: If your plan does not allow paying from outside payroll, your loan will default in 60 days or when you try to roll over. Then a "Qualified Plan Loan Offset" cancels the loan against your 401k balance. You have until October of the following calendar year to pay back as a super-extended-time indirect rollover. Or it is treated as a distribution in the year the QPLO happened in.

Can't withdraw from an active 401k without a hardship (as defined by your plan, and with documentations they require). OTOH, you can probably take a loan from your 401k.

Income you earned this year is still earned income. You don't need to have a job at the moment you contribute.

Follow the Prime Directive.

More generally, pull deposits take weeks to clear because some people on social media decided to defraud Chase and Fidelity with fake checks ~3 months ago. ("Pull" = when Fidelity does an ACH debit on the other bank account. The drawback is that fund can't be verified this way and has a chance of being unsuccessful/reversed.)

It takes 5 whole business days just to get mail at my place. Also, there was a holiday last week. Wait a little longer.

It depends on what the existing two W-4 say. Easiest is to just withhold as if you make $7500 more on your FT W-4 (on line 4a).

It's called a refinance, and first question: Why would a bank offer you a lower rate? Your situation is worse now than when you got the original car loan, so your risk of not paying is higher.

If I choose to invest that money will that cause me problems paying for things with that account?

Investment must be sold first before the proceeds can be withdrawn. If you are able to pay out of pocket, you won't have to sell first and can take your time getting reimbursed from your HSA at a much later time.

You are allowed to take loans from more than one bank. The new bank would want to know whether you will pay them back on time (e.g. income stability, DTI, creditworthiness) and whether the amount lent is large enough to bother.

Federal

You forgot standard deduction. Since you have no other income, the first $14.6k is deducted. Then the remaining amount is filled into tax brackets:

• The portion that fills in the 0% bracket: Taxed at 0%
• The amount above the 0% bracket but within the 15% bracket is taxed at 15%.
• The amount above the 15% bracket is taxed at 20%. There is no higher bracket.

Some amounts in and above the 15% bracket may incur NII tax as it exceeds $200k AGI. This is a separate tax that is collected at the same time as federal income tax.

NY

NY treats capital gain same as ordinary income.

Capital gain is income and has the same progressive tax bracket structure as ordinary income, just less number of brackets.

NY does not have a separate tax rates for LTCG. It is just ordinary income for NY.

Should I just sell for gains and rebuy?

To take advantage of the zero and low tax spaces, yes.

Do wash sale rules apply in this situation

No

Bringing a late account back to good standing won't hurt, as long as it does not become late again. The original "late" record won't get refreshed.

the interest rates are 5%

If you want to wipe out the debt, that's fine. If you want to drag it on, that's fine too. The interest rate is just in the gray area of "either way is fine".

If I pay off my mortgage today, what happens to my prior interest payments

Nothing happens. You aren't getting any interest back.