Unanswered Tax Questions

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Personal Taxes

Can i extend filing Federal taxes a 2nd time?

I requested an extension for my 2022 taxes. Can I extend it again? Do not have all info yet. I have paid same amount as 2021 yr, though income is less now & a refund may be due.

Asked Monday, May 15, 2023 by Margaret S.
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Personal Taxes

Health insurance premiums

The Main Question: If you pay for your health insurance premiums out of pocket (post tax) as a W2 employee, are you allowed to deduct the premiums if you take the standard deduction? If not, why? Surely this disadvantages W2 employees that aren't on employer health care as those that are have their portions of the employer health care premiums taken out pretax as such have a tax break build in. I am a PhD candidate. During the first two years of my PhD, I paid for my health insurance premiums, which were billed to my bursar account, in one lump sum. However, this year, I decided to take advantage of the offer from the graduate school and have my health insurance premiums deducted incrementally from my paycheck. When health insurance premiums are deducted from the paycheck, they are taken out on a pre-tax basis. My health insurance premiums do not appear anywhere on my W2 form. My W2 only includes basic information such as wages and taxes withheld. That's it. If I were considered a "proper employee," these premiums would be reflected in Box(es) 12 of the W2. My 1095-B has only proof that i am insured, and has nothing that says how much premiums were. So, my concern is whether I am inadvertently misleading the IRS by receiving a tax benefit that isn't reported. Did I miss out on any tax benefits during my first two years or is this a tax law that specifically benefits those with employer health insurance plans? Or could it be a combination of both?

Asked Monday, May 15, 2023 by CJ A.
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Miscellaneous

Inherited annuity

Will I have to pay taxes on inherited annuities? Is there a way around it

Asked Sunday, May 14, 2023 by TIMMRA H.
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Deductions and Write-Offs

Home Office to Main W2 job office, can I write this off?

Can I deduct my drive to my W2 job from my home office if I can classify an area of my home as an office? Then it becomes trips between offices, which is deductible. I do this for my side business, with my office in the home going to my warehouse. What is preventing me from being able to do this with my drive to my W2 job from my home office?

Asked Sunday, May 14, 2023 by DAKOTA N.
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Small Business

FHA loan, my name on wife and I's business

Hello, my wife and I are photographers. The name of the business is in her name. She bought a house 5 years ago FHA and now I am trying to buy a house FHA. The bank accounts the income goes in is in both our names. The tax returns name me as primary borrower. What is the best way for my name to be put on the business for loan purposes?

Asked Saturday, May 13, 2023 by glen w.
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Where is My State Tax Refund?

Never received

I have not yet received my taxes nor my stimulus checks none of them

Asked Friday, May 12, 2023 by Audrey L.
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Tax Forms

Twitch talent agency

On twitch, my talents are working as independent contractors under my sole proprietorship. If they swap their payout and tax onboarding information to being under my individual name and EIN, is that sufficient (they are working under my company, which does not have a larger LLC), or should be paying me separately for the services to avoid any issues and misunderstandings

Asked Friday, May 12, 2023 by Trixie Z.
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Retirement

Roth Ira

I opened a Roth account March 2019 with $85;000. I know there is a five year rule. I am 85 years old. Should I be taking distributions? Also, can I take withdrawals before the five year date? Thank you

Asked Friday, May 12, 2023 by Naomee G.
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Personal Taxes

Illinois employer did not withhold state taxes (mandated withholding state)

My Illinois employer has not withheld any state taxes from my pay. Now I owe $850 to the state. Are they responsible since they are required to withhold? Thank you

Asked Friday, May 12, 2023 by Lora A.
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Miscellaneous

HOW MUCH MONEY CAN I WITHDREW FROM THE BANK WITHOUT THE BANK REPORT IRS

HOW MUCH MONEY CAN I WITHDREW FROM THE BANK WITHOUT THE BANK REPORT IRS AND HOW MANY TIMES I CAN WITHDREW WITH A MONTH OR HOW OFTEN SHOULD WITHDREW WITHOUT BANK REPORT TO IRS I ONLY HAVE A CHECKING AND CHECKING

Asked Thursday, May 11, 2023 by GWENDOLYN M.
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