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

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