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Dave CPA
Dave CPA, Accountant
Category: Tax
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Experience:  Vast knowledge within the accounting/tax industry
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Is anybody here a tax expert? Is this forum confidential?

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Is anybody here a tax expert? Is this forum confidential?

I'm a tax expert and your identity is only revealed to use asCustomer I can try and help, but what is your question?
Customer: replied 5 years ago.

I have not filed taxes since 1999. I have little or no records. How can I clear this up?


This is not an easy situation. You should find a reputable tax professional in your area that has experience with matters such as yours. They should be able to help negotiate an offer in compromise to help with the tax liability depending on your situation. An offer in compromise allows you to settle your tax debt for less than the full amount you owe. It may be a legitimate option if you can't pay your full tax liability, or doing so creates a financial hardship. I have enclosed a link about an offer in compromise below from the irs.

I can't stress enough that you need to reach out to a tax professional that can sit down and help you with this and work though every year with you. If you do this, I know in the end you can get through this.

Please let me know if you need more clarification. Regards Dave
Customer: replied 5 years ago.

Thank you for your excellent advice. I would like to bend your ear a little more.


I will reach out to an expert. It is my understanding that they have records of case law that can assist me.


First of all, I made a few hundred thousand for a few years in a business. But I also invested $600,000 in that business and always took a position that investing in businesses was my business so I could take ordinary losses for losses. I got the investment money from inheritance and loans and stock market gains but I don't have good records. After this I became very sick (or perhaps during) with bipolar disease and recently severe diabetic condition. I also had to pay my ex-wife all my money because my support was set at conditions when I was making a lot of money ($6K a month and then raised to $10k a month), I could not get it reduced because there was at that time no diagnosis of bipolar condition.


I only received that diagnosis in jail by a board certified psychiatrist when I was there for 6 months for failing to pay child support, and then got on the right medicine. The Judge's doctors completely missed the problem.


Since then I have made a small living teaching - sometimes 20k to $30k,. Living with friends. Occasionally being homeless. I did have one year of a good job but that company (an Internet company) closed.


This year better maybe $80k as I have drawn a better following and my medication is working better so I can work more. At this point, assuming my health continues to get better.


I want to clear this and be able to say I have filed returns. Will this accomplish so I can say I have filed returns when asked by regulators or the government so I can get back into finance or allow me to marry a wife not from the U.S.?


I want to know if it is likely I will go to jail (again).


Whatever number they come up, I won't be able to pay it at once as I have only $10k in savings and I need that money for my business and daily expenses. So how they do a payment plan.


Thank you for your attention.

After reading your circumstances, it sounds like you have much going on. That is why it's important to deal with a good tax professional, whom can file your taxes for the prior years in an accurate manner. This will make you clean going forward. I think if you come clean with the IRS and work out a payment plan the probability of going to jail is small. After all the IRS can't get their money if you are in jail. The payment plan is very common and they make installments based on your ability to pay. Let me know if you need anything else.
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