The biggest determining factors, in my mind, are what city would you be happiest in and how much money do you have to put towards your upfront costs.

It's realativley easy to get started, low downpayment owner occupied loan, and it eliminates your single biggest monthly living expense: housing.

@James Rador if $200 is your biggest concern, then not a big issue in my opinion.

This is the biggest downside to a Roth IRA in my opinion.

Yes it's possible, but zoning and utilities could be your biggest roadblock - not to mention water in basement as mentioned by @Dave Spooner.

Being prepared to pay the mortgage off if called due is my biggest concern.

@Hillary Windrem we flip exclusively remotely and the biggest challenges has been accountability and processes.

If you're looking for a buy and hold, you may want to consider looking at macro trends like population shifts, landlord friendly states, states with low taxes or good incentives to bring in businesses, etc.

The biggest thing you have to consider is your exit and unless you can make this a really nice small park or group it with other assets as part of a package it will be hard to exit any time soon. 

My biggest draw back with Stessa is that you cannot accept payments through it or communicate with the tenant in any way.