Landlord drives by on the 1st of each month and collects.

Find something in state or the next state over that is in driving distance. 

I'm in a drive to beach market so I'm on it but I would think college towns, mountains etc. might be similar.

I had a case where it looked like the umbrella policy could get used but 1) ended up Not being needed 2) was vehicle related, not RE related.Our Son’s girlfriend was driving one of our vehicles and got into an accident.  

For the latest rental market reports see this link:  https://drive.google.com/drive/u/1/folders/1NKewu6hPV_LrVR3G...'

Alternatively, you're a 5 minute drive to the resort.

@Wade Wisner Jacksonville has seen some significant changes over the years, with pockets of revitalization and a strong influx of new buyers driving growth.

However, I live close-by (30 minute drive), recently retired from my day-job, and if the loan is not too large, I might be willing to do a deal just to learn a bit more about another side of RE.  

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

Driving around the neighborhood over time, I saw the same van at a few other houses.