I think if one can remove the prospect of his own occasional use of the property for his own leisure, then longer term rental is probably less stressful because you don't have to deal with the routine cleaning. 

If your tenant cannot handle routinely sending you checks in the mail that don't bounce, you can and should do better.

After moving in, I painted the exterior, made a few cosmetic updates and actually reconfigured the doorway for more space parking.

They keep tight control of their rental properties after their cash is out of them and they routinely check up on any property managers they hire.Go turnkey or a similar strategy, and whatever you do, don't fall for the guru line that wholesaling is the right way to get into real estate with no money down.

I still routinely buy 7.5-9 cap deals (with some rent increases) just takes bigger properties and jumping on properties when they come up. 

Do some cosmetic upgrades (paint, countertops, cabinet hardware, appliances, flooring - if allowed - see governing documents, lighting, etc.) to attract quality tenants, command market or above market rents, gain appreciation; 5.

@Jon AllenThankfully, this turned out to simply be a top-down cosmetic renovation on the interior.

I assume he could deal with my estate if I were to die without having sold it to him.Is that something that is routinely done?

The exterior needs cosmetic work as well.

The exterior needs cosmetic work as well.