Being clear about what you want to do from the start not only helps you stay on track, but it also makes it easier to spot problems or delays before they happen.I totally agree that talking to people is important.

They average 4-5 night stays, keep in mind im not in a vacation hot spot.

@Marc Shin ask every guest that stays with you for a 5 star review after their stay.

I would consider staying with your parents and investing in another market that stretches your dollar and covers the cost of a professional property manager.

For instance instead of having to stay glued to new listings, find the ones that show potential, then estimate rent, then put them in your calculator, then look at comps for ARV, then finally calculate offer price etc. 

For Airbnb, do i allow STR stays for the next three months and then block out the calendar beyond 3 months for MTR stays?  

We have told my ex-wife that we are willing to let her stay in the house for a time but she needs to pay rent.

You need to make sure you understand every detail: how the lease terms adapt over time, what kind of negotiating room you’ll have when it’s time to renew, and whether lenders in your area are open-minded about financing these kinds of ground leases.

If you are going to get your license in Virginia I would plan to stay there for a decent bit(5+ years).

Tenants prefer detached housing over attached housing and stay longer.