We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

I’ll cover a few of those for you as well as try to offer some advice.

Once I get a few stable long term rentals maybe consider looking into such properties and cover aspects I am able to confirm. 

In other words, your renters have covered a majority of your costs of ownership this year, including covering your debt, and you have to put some additional money in, which raises your cost basis.

Hopefully the deposit covers Jan rent, make sure you give them an itemized list of the money owed to you for any damages or unpaid rent. 

No amount of insurance covers the personal loss.2.

Maybe even offer to cover some closing costs to sweeten the deal if they’re stuck on a higher price.

Hostfully seems like it will cover the basics we need, plus it has some unique features that others didn’t offer.

I often have tenants who don't pay the last month's rent because they think the security deposit will cover what is owed. 

IF you plan on going back someday, and this is the home you want to move back to, then renting it would be a good idea as long as you estimate that it will cover itself, or preferably, cash flow, which it appears that yours will at @ $2K or so per month (after expenses).