USA Estimated Taxes Queries for Rideshare Service


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Hello Everybody!

I am in my late 30s and have just started providing Rideshare transportation service via one of the companies many here most likely have heard about. I understand that I am considered an Independent Contractor and thus am expected to pay quarterly estimated taxes. However, I have a very unique personal situation which I will address, and accordingly have come here to seek advice on how to do everything appropriately.

Over the last fifteen years, I have been unable to work due to illnesses. I have not received one cent of charity/public assistance, and have sustained myself on the generosity of family and during the past five years through income derived from a brokerage account inherited through a relative. While that income is approximately $20,000/year, I have been running a deficit EVERY year because of property taxes I have been paying for myself and my disabled mother, an IHP insurance plan which I pay 100% of the monthly premiums, and other luxuries like food, gasoline, heat, and utilities. As such, I essentially live on a thread-bare shoestring and can barely afford the above expenses, let alone whatever the IRS and/or the State of New Jersey may feel I should pay in taxes. The run-down house I reside in which was purchased over forty years ago by my parents is owned free-and-clear and I own my own car, also free-and-clear. Needless to say, this situation has been demoralizing and personally embarrassing. It is also financially untenable as a going concern.

While I am still afflicted by the same illnesses that have plagued me, my current medication regimen has brought me to a point where I can now perform the level of work that Rideshare requires. The combined income realized from the brokerage account and the Rideshare work appears at present will help to alleviate my financial worries and restore my dignity. However, the taxation requirements for both the Federal and State levels are a little perplexing to me, and I don't want to evade or otherwise run afoul of tax laws due simply to ignorance.

I have several questions regarding how and when to file, claim deductions, and whether I should itemize or take the standard deduction and if I can do so on both Federal and State returns. And should I include the dividend and interest income from the brokerage account on the quarterly filings or just in April. Obviously, I do not have a prior-year return to compare for future filings. I would be willing to consult a CPA, but I am concerned that the expense of such professional services on a quarterly basis would be prohibitively expensive and likely an unrecoverable expense. Essentially, until I earn substantially more through my new Rideshare work, I cannot afford any sudden big-ticket expenses. I am already paying off existing medical debts which amount to approximately $3,500. I keep records of all my expenses.

Please advise if I have posted this in the correct forum, and if so, I would be happy to provide any non-identifying details in order for you to best assist me. Thank you so much for affording the public this forum and I look forward to chatting with all of you soon.
 

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