However, we found receipt management (downloading emails and pictures and saving them to Google Drive) to be so cumbersome and decided to join QBO train.

Set your standards up front.Raise the rent to the market max and the difference will cover the deposit in 12 months or so.

As I mentioned above, the risk of being sued, found guilty, and fined more than your insurance will cover is almost non-existent. 

Her retirement income would be used to cover the mortgage.I hope this gives you an idea of my plan.

Also, looking at the bigger picture, if this remains contentious, good luck getting him to come back to address any warrantable repairs etc.

Your insurance may also not cover you or your tenants. 

You get the picture. 

@Paw Nouri Maybe in your area they will cover damages but not in Maryland.

I have high revenue from my rentals and have diversified other investments that cover my lifestyle.  

Make sure you have adequate reserves to cover unexpected emergencies.3) Time-intensive - If you live on-site you're a live in property manager on call 24/74) Legal issues - know the max occupancy laws for your area.