No personal income or tax returns are required.

Some are owned by my ROTH IRA and are making tax free cashflow.

Quote from @Michael Overall: Good day, If an investor has 10 rentals and wanted to over time sell them and put the money tax free from a 1031 toward a large purchase is there a process to do that? 

Yes, you will have to file the partnership tax return.

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.

So, in your considerations, I would park right there for a bit and determine how this would look for you.Since you have about 2.5 years to think about it before you would need to spring into action to take advantage of the rollover for tax advantages, maybe you try on a rental and see how it fits. 

.: Stessa isn't good for keeping track of tax deduction items.Stessa was designed to just look at P&L.

Ensure you collect a proper security deposit (typically one month's rent in Florida) to cover potential damages.Your plan to increase rent next year makes sense given rising costs (taxes, insurance, and maintenance).

Then purchase a Note, generate $250 - $300/mo tax free!

Going direct saves you and the seller money, giving you a lower cost to entry which helps all your numbers, but you have to put in the extra work to find that deal.