Paying my back taxes - 2014 - 2018 ...offer in compromise?

[georgeworld2022]

Hi Guys, 

1. I have not filed taxes for 2014-2018, and I think I will most likely owe late fees and penalties.  

2. I just finished 2014-2018, and I am looking at the printed out tax returns on my desk.

3. My next step is to mail these into the IRS with a verified delivery.

4. I have recently got a $100,000 SBA loan, and I am planning to just use some of that money to get current with my taxes. 

5.  Would recommend that I send a separate check for the 2014, 2015, 2016, 2017, 2018 all in the same envelope with a check for the amount Turbo Tax says to pay for each year individually?  Or is there some benefit to decreasing the chance for an audit, for example if sending them one at a time, one per week, for example?   Because if one IRS agent received all years all at once, I think this might lower the chances of triggering an audit?  I don't think there is any reason to be worried about an audit, but I just really don't have time, in running my business and taking care of my mother, etc, it would be a headache to get audited. 

For example, if there are 5 IRS agents who each receive a different year, and looking at the returns, etc?   is it a better idea to send a check for the amount owed for each year with my tax return, or is it better to NOT send a check, and wait the IRS to adjust the automatic return they filed on my behalf because I did not file (which has some ridiculously high amount)?  I have a hunch that if I sent full payment for each year (include a seperate check for each year), the IRS might be more lenient with the penalties?  What do you think? Or should I not send any payment and just wait and see what happens and try to setup offer in compromise?  Thanks in advance for your help.  

George

-self employed web designer averaging $150k per year

-single

-no hardship besides just trying to build my business

-I live in California

-No property

-No assets

-very simple returns

-no levy yet 

-I had a payment plan setup in 2015 which I defaulted on

-I am current on my 2019 and 2020 taxes

-2016 is my highest income year

[rjs]

IMPORTANT - Mail each tax return in a separate envelope with a separate check. Never send more than one tax return in one envelope.

Your mailed tax returns are not processed by IRS agents. They are handled by data entry clerks who just type the information into a computer. If you put more than one tax return in an envelope, it's almost certain that only the one on top will get entered, and it will be as if you never filed the others.

You must have already received some IRS notices. Respond separately to the most recent notice for each year. If your response to a notice includes a tax return, follow the instructions in the notice for where to send it, which is probably different from where you would send a tax return for the current year. Mail each envelope by certified mail with a return receipt so that you have proof of mailing, tracking, and confirmation of delivery. Keep a copy of everything that you send.

The IRS is severely backlogged this year. You should expect it to take 6 months or more before you get any response to any of the tax returns that you are mailing now.

An offer in compromise is not appropriate at this time, and may never be appropriate for you. One of the requirements for an offer in compromise to be considered is that you are unable to pay what you owe. That does not seem to be your situation.

You do seem to have quite a mess on your hands. You would probably benefit from consulting an experienced tax professional instead of trying to handle it all yourself. Talk to the tax pro before you send any tax returns or other responses, but try to make sure that you respond to any notices by the deadline in the notice.

[Mike9241]

here's a link to the IRS OIC calculator.   this is a tool to see if you qualify not an actual offer.  however, even if it's concluded you do, I agree with RJS seek out a pro. 

https://irs.treasury.gov/oic_pre_qualifier/