I believe the older vacation homes that have not been brought up to date will really struggle with occupancy and / or rates. 

Tuscaloosa is particularly interesting—it’s a growing college town that’s home to the University of Alabama’s flagship campus.

Pay it off and then buy a new primary and turn your current home in to a rental.

G'Day Alejandro,As a few have already mentioned, take a peak at Toledo also.In my opinion lower potential for long term appreciation but solid/"boring" cashflow.I prefer my portfolio to be "boring" but cashflowing lolLow entry points (Sub $100,000), high rents (Above the 1% rule).Blue collar working class decent folks that will stay and pay.Depending on the area but no derelict homes, yards well kept, cars with wheels and all tenants are employed.Plus, all are sophisticated enough to pay rent online so property management doesn't have to collect rents with bullet proof vests and shot guns lolI'm bias toward Toledo but it's worth considering.Wishing you much success

My wife and I own a single-family home in a top school district.

Our strategy is looking for multi-family homes to purchase and hold as option 1. 

Also I am living in the property but my registered address is still at my other home.

I learned this when I bought 12 new builds for GOZONE tax bene's really nice brick homes in best part of town but values just did not rise enough so by the time i had to change everything out and pay sales commish it was break even at best..

Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.I ALMOST understand the rental arbitrage strategy if building a company scaling with say 30 + units and looking for high short term cash flow.  

I am five months in quieting a title on a home/property that was initially obtained by my father in a tax sale.