He told me he owned a few mobile home parks in town (they were large and had high lot fees) and this is what sparked my curiosity.

@Ed Lopez what controls do you have over what they decide to do?

I'm in a beach area where Sat to Sat rentals have been traditional for 100 years, but not any longer since the rise of Airbnb (and less control by local property management companies).

I'm sure there are many more experiences where the contractor hasn't fulfilled their scope of work and gotten away with rushing the project to meet the deadline, And, I don't want to be as naive to say that I'm that 1% who can have complete quality/operational control, but I'm confident I can establish a system and hire independent inspectors to review the contractor's work. 

All the friends I trust were out of town or married, and I was done living with strangers. 

Hey Santosh,As of right now you're extremely exposed regarding insurance and I'm going to assume legally as well.If the home isn't registered as a legal multi-family with the town that's something you'll have to correct ASAP and make sure the home is up to code.Insurance wise as soon as they find out what you're doing they'll cancel you as the risk has changed from a single family owner occupied home to a multi family owner occupied home.

I hope you or someone is at least keeping an eye on your properties for break ins, squatters, roof leaks, temperature control, frozen pipes (if in cold climate), if you have a basement and sump pump goes out leading to water damage etc.I just talked to two investors in California that have let their properties sit vacant (no mortgages so paying property taxes and insurance).

There are towns that are not too far where there could be some options for you, but I would start going to real estate investor meetups and pair that with books and podcasts.

Hi Levi - I'm also looking into OOS and heard about Tuscaloosa, AL being a good college town to invest in.

There's lots of opportunities in developing neighborhoods, but also seems a bit saturated at the moment.Also, definitely budget security (remote control cameras, alarm system, etc.) for your properties, as there are a lot of people who occupy themselves by breaking into houses and stealing anything they can sell.Lastly, there are a ton of contractors looking for a quick buck.