For it to work for both parties you will have to do a little more hand holding and one on  one involvement than you would for a normal rental.  

There is a legal concept that when a contract is ambiguous that it will be interpreted in favor of the party that did NOT write the document.

I then had to resync it all over again.Even QBO has sync issues but at the very least they make it very obvious that it isn't syncing lolI think the issues is more of a 3rd party that they use like Plaid and others

Call previous landlords...was there police calls, missed rent payments, parties, complaints, etc. 

Then there are other items that are negotiable in terms of marketing to get the place rented or at time of signing lease between the two parties.

Another may see it from the perspective that they've been getting a free ride all this time and now the party has ended.

Without knowing the appreciation in the area you bought, that part is hard to answer, but just given your numbers I would definitely sell.

Obviously would change from person to person, but I'm curious what people have used before that has been effective for both parties. 

That said, in Florida, the parties can enter into an agreement that qualifies the tenant's and landlord's use of the premises.

For my part, I wouldn't call anyone who started out with "don't waste my time."