Haven't filed 2019 yet

[mytoiletsclogged]

The short version of this is how much trouble am I asking for to wait until March or April of this year to file my 2019 return? I know if I owe there will be late fees and late filing penalty and interest, blah, blah, blah...

I'm in a situation where I am and have been scrambling to get packed up and moved out of state, and I haven't filed my 2019 return yet. I had withholding from my paycheck when I was working and I paid estimated tax payments for my side business income--I did request an extension last year and I believe I will have a refund coming.

I got a delinquent return letter from the IRS, and I'm torn at this point whether to take the time right now to just knock it out, or finish the repairs on my house to put it on the market so that we can get moved. Either way I have a ticking clock. I just need about another month to do some work on my house and pack up and haul to our new home. I won' bore you with details but I have been delayed a number of times due to appliance breakdowns that I had to fix, and COVID hasn't helped. We'll be renting there for a while so I will have time then to sit down and grind out this tax return.

Even if I took my stuff to a paid preparer, I would have to take time to organize everything better and generate some summaries of my business stuff from receipts, and do some scrutiny on things I sold to dig up the cost for COGS. I am really reluctant to go to a paid preparer because I've done that twice in my life at different time, and they both screwed it up--and they were CPAs, not H&R Block either.

[SamS1]

If you received a delinquent return letter, you are already moving up the IRS food chain.  If you don't get something in soon, the IRS will prepare what's called a substitute return and assess you the tax they have calculated.  A substitute return is prepared based on the information that has been reported to the IRS.  Informational return info form W-2s, 1099-MISC, 1099-INT, DIV, B, etc.  You mentioned you have a side business so in the substitute return prepared by the IRS, no expenses would be used to offset your business income.  Your tax billing will be crazy high and not correct.  That being said, the IRS is in the same boat as everyone else when it comes to Covid.  Many agents working from home and no real phone support.  This might slow down the collection process for your 2019 return.

You will need to prepare your 2019 return using the desktop software if you decide to use TurboTax and mail the returns in.  The online product is only for the current tax year.  Here is a link from Amazon for the 2019 Software.  There are other considerations to get your return in soon like the 3rd stimulus payment coming up.  You will want to something into the IRS to qualify for this payment.