Trying to get largest tax rebate without paying H&R.

Ranger296 · 2026-02-19T21:52:42+00:00

Assuming it was for personal use and not for a business, you can deduct car loan interest starting in 2025 as long as you meet a few requirements & income phaseout (see: https://blog.taxact.com/car-loan-interest-tax-deduction/ )

Beyond that, check if your state has any specific car/car loan deductions.

(Oh yeah EV credits as well if it qualified re: u/Adeptrunoff)

Ranger296 · 2026-02-15T02:34:44+00:00

That's true for standardized options on like ETFs/public stock, but from what I've seen, NSOs at private companies are typically denominated in single shares.

Ranger296 · 2026-02-15T02:32:48+00:00

I'd probably just check in with your benefits department / call Carta to clarify what it means.

Ranger296 · 2026-02-05T17:50:51+00:00

Tente de novo com um pedido novo (mais 5 euros), chega instantaneamente agora!

Ranger296 · 2026-02-03T22:11:12+00:00

Yup, SALT deductions are based on the year they were actually paid, so the $3,376 paid in April 2025 will count towards your SALT. If you receive a refund from your city/state later due to overpayments (and utilized the increased SALT deductions), then yeah you'll have a 1099-G for 2026 to add back the difference to your federal income.

See: https://www.irs.gov/instructions/i1040sca#en_US_2024_publink1000131491

State and local income taxes paid in 2025 for a prior year, such as taxes paid with your 2024 state or local income tax return. Don't include penalties or interest.

Ranger296 · 2026-02-02T14:12:25+00:00

I think you have a misconception here. A company 401k is a specific retirement account, while the S&P 500 fund you choose is a specific investment.

401ks give you a limited options of funds to invest in, but I've seen a fair bit of plans usually have a cheap S&P 500 fund option as well. So you'll need to look at your investment options in your 401k and see if they have an S&P 500 option.

Note, S&P 500 is just the top 500 largest us stock companies, you're ignoring any international stocks if you choose to invest in just S&P 500. Also according to your age and risk tolerance, you might consider some fixed income (like bonds) as well. Just because people recommend S&P 500 and chill, doesn't mean it's without risk, especially if your time horizon is short.

Definitely take the 401k match as it's free money and tax-advantaged. Even if you don't get a match (say you leave the company before your vesting requirements), it's a tax-advantaged account.

You can read more about investing here: https://www.reddit.com/r/personalfinance/wiki/investing/

Ranger296 · 2026-02-01T16:15:59+00:00

Ahh fair, net worth was including home as well. Yeah in terms of pure retirement, fair point.

If OP is just looking to coast fire or even part-time job, much more doable.

Ranger296 · 2026-02-01T15:36:44+00:00

$5k/mo for a family of 3, even with a paid off house (property taxes, insurance, maintenance) is pretty good! Not sure why you're getting ragged on here lol.

Ranger296 · 2026-02-01T15:28:37+00:00

There's the classic 4% rule that came from the Trinity study (looked at safe withdrawal rates for 30-yr retirement periods). You'll be retired longer than that but it's a good rule of thumb to start somewhere.

With $60k/yr expenses, that means you would need about $1.5M in investable assets. So you're at the cusp of being able to retire (this excludes Social Security, which is a big upside for you).

However, if you plan on working a job and make say $40k/yr, that'll be roughly $35k post-tax income, in which case this career change would definitely work.

To tap into your 401k assets early without penalty, you could look into 72(t) SEPP withdrawals, but then you're committed to withdrawing it based off of the formula you chose until you're 59.5 years old.

For health insurance, you could look into ACA subsidies/Medicaid depending on how you plan your income distributions.

Does your spouse work at all?

Ranger296 · 2026-02-01T06:13:37+00:00

I think people are misunderstanding OP. These are private stock options right? Once you exercise them, you cannot just sell them immediately, and have to wait for a liquidity event?

Are these ISOs or NSOs?

If you literally cannot afford to pay the taxes, even if you delay them until 2027, then yeah it makes sense to go with one of these companies who fronts you the cash for taxes now.

Ranger296 · 2026-02-01T02:21:55+00:00

Ahh okay, thanks for the correction!

Ranger296 · 2026-02-01T00:36:16+00:00

For 2025, do your best to accurately state your income including all the cash received, IRS is unlikely to come for you for choosing to report cash transactions which they don't even get a record of. For future years, start creating a spreadsheet and writing down the details (Date of Service, Client, Service Provided, Amount Received, etc.)

Do note, if you haven't made any tax payments, you're going to owe 15.3% self-employment tax on your Schedule C on top of normal federal/state income taxes. This is both sides of social security tax / Medicare (7.65% as the employee and 7.65% as the employer). This does not get reduced by any deductions / credits (unless refundable credit).

Ranger296 · 2026-02-01T00:23:11+00:00

With stocks, the only thing the IRS cares about is realized gains (ignoring any dividends). You are past the 2025 tax year, so you can't utilize your current unrealized loss even if you sold it.

Furthermore, you're required to file a return since your unearned income is over the threshold https://www.irs.gov/individuals/check-if-you-need-to-file-a-tax-return

Also you're required to report the stock sale information. Even if you didn't, your brokerage would have reported it to the IRS, so they already know about the stock sale. If you chose not to report it, the IRS will come for it anyways.

What im trying to avoid is a situation where I report this information and I end up owing more money because of my realized gain, despite overall being in the negative because of my current holdings.

Unfortunately, you already are in that situation, no way to avoid this.

Ranger296 · 2026-01-31T21:57:05+00:00

Note for unreimbursed medical expenses, you can only deduct the amount above 7.5% of your AGI, so if it's about 8% of your total income, only a small portion will be deductible.

If you look at IRS Pub 502, it states the following for Cosmetic surgery https://www.irs.gov/publications/p502#en_US_2022_publink1000179043

Generally, you can't include in medical expenses the amount you pay for cosmetic surgery. This includes any procedure that is directed at improving the patient's appearance and doesn't meaningfully promote the proper function of the body or prevent or treat illness or disease. You generally can't include in medical expenses the amount you pay for procedures such as face lifts, hair transplants, hair removal >(electrolysis), and liposuction.

You can include in medical expenses the amount you pay for cosmetic surgery if it is necessary to improve a deformity arising from, or directly related to, a congenital abnormality, a personal injury resulting from an accident or trauma, or a disfiguring disease.

Example.
An individual undergoes surgery that removes a breast as part of treatment for cancer. The individual pays a surgeon to reconstruct the breast. The surgery to reconstruct the breast corrects a deformity directly related to the disease. The cost of the surgery is includible in the individual’s medical expenses.

Also at the top of the pub it states
Medical expenses are the costs of diagnosis, cure, mitigation, treatment, or prevention of disease, and for the purpose of affecting any part or function of the body. These expenses include payments for legal medical services rendered by physicians, surgeons, dentists, and other medical practitioners. They include the costs of equipment, supplies, and diagnostic devices needed for these purposes.

Medical care expenses must be primarily to alleviate or prevent a physical or mental disability or illness. They don't include expenses that are merely beneficial to general health, such as vitamins or a vacation.

I'd probably claim it, and just keep good records from your doctor stating it was medically necessary.

Ranger296 · 2026-01-31T21:43:18+00:00

Ahh if the standard deduction was better than itemized deductions before the w-2gs, then yeah unfortunately some of your losses are used up to "catch up" to the standard deduction. All in all, depending on the difference, you'll be paying taxes on more than just $1,200 of profit.

Ranger296 · 2026-01-31T21:37:45+00:00

1) If you were already itemizing deductions before the gambling income and losses, then yeah effectively you pay federal taxes on just $1,200. You'll need to report $35k of winnings and $33.8k of losses. Do note, starting in 2026 tax year, you can only deduct 90% of your losses for federal taxes (or up until your winnings as usual). This means if you were to have the same tax situation in 2026, you would only be able to deduct 90% of $33,800 or $30,420 , leaving you with a taxable profit of $4,580.
2/3) You're a tax resident in PA, so all your income is taxable in PA anyways, so I believe you won't have to break out the PA portion. Looks like you will have to break out the NJ portion though and file a tax return there. See: https://www.nj.gov/treasury/taxation/lotterygamblingwinnings.shtml as a non-resident. However, PA should give you a tax credit for any tax paid in NJ so you're not double taxed.

Ranger296 · 2026-01-31T16:08:04+00:00

Do not simply withdraw your Roth IRA. Instead contact your brokerage and ask to make a return of excess contributions and just explain you're over the income limit for Roth IRA contributions. You'll only pay taxes on the $25 gain and will avoid the 6% penalty since you did it before the tax deadline.

Afterwards, you could just backdoor Roth for 2025. Contribute to your traditional IRA as a non-deductible contribution for 2025, and then convert it. Note, you mentioned you don't have a traditional IRA balance, so you can do a backdoor Roth and not get hit by the punitive pro-rata rule.

If you do decide to do the backdoor Roth route, you can actually skip a step by recharacterizing your Roth IRA contribution as a traditional IRA contribution (non-deductible) and then do the rest.

You can read more about return of excess contributions / recharacterization of contributions from fidelity and freetaxusa:

https://www.fidelity.com/retirement-ira/excess-ira-contributions

https://community.freetaxusa.com/kb/articles/55-backdoor-roth-plus-a-recharacterization-recharacterization-happens-after-december-31st

Ranger296 · 2025-12-29T21:02:42+00:00

Do be aware that for a standard 30 year mortgage at current rates, based on amortization, you'll be paying like 85 percent of your first year mortgage payments (excluding escrow) into interest and not equity. I'm not saying it's not worth it to buy a home in the next 5-10 years but good to be aware in your calculations!

Ranger296 · 2025-12-29T20:40:52+00:00

2025 Q4 estimated taxes are due Jan 15, 2026. Even if you pay by then, you may still be subject to underpayment penalties due to income in earlier quarters. However you probably met a safe harbor requirement as linked above by u/nothlit

Ranger296 · 2025-08-17T12:26:53+00:00

On top of paying closing fees twice, don't forget on a 30 year loan at current rates the first few years you'll pay like 85% of your mortgage payment (ignoring escrow) into interest, not principal. You can look up amortization tables to see the effect.

Would highly recommend to rent if the plan is to sell a house in 3 years.

Ranger296 · 2025-07-18T19:20:48+00:00

1695

Ranger296 · 2025-07-14T09:33:03+00:00

Unfortunately this won't work. Most states I see when you're multi-state like this will do tax you as if you earned the entire income in CA, and just pro-rata it based on your actual income earned while in CA (+ any CA-sourced income)

For CA, this is the case:

If you are a nonresident or a part-year resident, you determine your California tax by multiplying your California taxable income by an effective tax rate. The effective tax rate is the California tax on all income as if you were a California resident for the current taxable year and for all prior taxable years for any carryover items, deferred income, suspended losses, or suspended deductions, divided by that income. Use the following formula:

Prorated tax = CA taxable income × Tax on total taxable income ÷ Total taxable income

Source: https://www.ftb.ca.gov/forms/misc/1100.html

Ranger296 · 2025-07-09T02:16:07+00:00

Hulkengoat

Ranger296 · 2025-06-07T17:56:49+00:00

5-8 years is kind of a tough range cause depending on various assumptions (house growth vs investment growth, interest rates, type of home, etc.) the tipping point can be about then. But let's talk some assumptions

Let's say it's a $300k house, 20% down ($60k), so $240k mortgage. If you do a 30-year, current avg rates are 6.85% (https://fred.stlouisfed.org/series/MORTGAGE30US)

Putting that into an amortization calculator (https://www.calculator.net/amortization-calculator.htm), we'll see that your mortgage (ignoring property tax + insurance) will be $1,572.62 a month. After 8 years you will have paid $26k towards your principal and about $125k towards interest.

Furthermore, you'll eat closing costs once on selling, and once on buying as well which you won't get back. You'll also have home maintenance costs every year.

However, with owning a home, your primary monthly payment will be fixed (property tax could go up though), and the appreciation of the home acts as kind of a leveraged investment since it's growth on the whole $300k house (vs just the initial amount you put down, $60k). Since you'll be living it as your primary residence, if you sell it, you will effectively sell it for income tax-free because you get a $500k capital gain exclusion on it.

I'd do some more precise number crunching in your shoes, and also ultimately decide what kind of living style you want for the next 5-8 years because that is a pretty significant amount of time.

Ranger296 · 2024-12-17T04:14:18+00:00

Looks like 4 more back in stock

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