Tenants in general are very “ monthly payment sensitive” so you should just keep your rates at the market prices and fix stuff when they break it .

@James Morin, I would address this question to a lawyer to be better advised as it can be a sensitive matter. 

@Michael Mumenthaler a lot of this is probably regionally sensitive, but I have never rented a unit in an HOA and not paid it myself out of the rent.

On the tenant background information however, you should at least be provided with the lease and the names of your tenants however, we nor most reputable PM's will share sensitive tenant background or contact information with owners.

I do like that that owners would like to become the tenants and believe setting up a mortgage servicer safeguards the original mortgage by ensuring it is getting paid. 

Neither my previous or new tenant are being too sensitive. 

If you own property you need to protect yourself, but only if you truly have a ton to protect and don't have enough up front (insurance, safeguards) in place to protect you.

The whole process has been a little sensitive only because I am trying to be fair but also make money/not lose money.

Make sure you have extra safe-guards in place though, i.e. a security system installed once you receive appliances, cage your AC unit, etc.

Here is my opinion for what it is worth: buying SFHs is very timing sensitive.