I paid it...Didn't  find a buyer and lost the deposit. 

Do a cash for keys deal and just try to get them out early… I’ve thought about offering that if they leave by the end of November (~60 days notice) that I’d give them November free + $500 in moving expenses and return of security deposit if left in good condition3.

Deposit AmountThose are the 4 items you have to play with that do the negotiating. 

You get an estoppel from each tenant saying this is how much rent I’m paying, this is how big a security deposit I gave, here’s who pays for utilities, when my lease ends, etc etc. 

My recently departed tenant's deposit was not enough to cover all the repairs (repairs NOT due to normal wear and tear).

So I made a compromise with myself, instead of putting that $100 directly to my principle, I'm opening a brokerage account that will have $100 deposited into it automatically every month and invested in index funds using dollar cost averaging method.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Are there deposits on file?

The information is provided in 'how to get your security deposit back at the end of your lease' language.  

If you're going for non full documentation loans then there are other methods to qualify as well (rental income/ bank deposits/profit and loss/no income/etc) but these loans have higher rates and costs typically.