But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

Just google the following: - special assessment - zombie condos - Florida condos (look for recent news)Since you are not living near the properties anyways, why not look in a landlord friendly state where the purchase prices are lower?

@Isaac TerryIn terms of it being worthwhile, just like most other markets out of state if the barrier or entry is too high where you live, the landlord laws are not favorable where you live, and you are looking for positive cashflow then Cleveland can be a good option.

I know in Philadelphia if I had a 2 BR house it would be viewed favorably by tenants who are seeking 2 BR living situations because most inventory will be apartment style living and for this reason would achieve a rent premium.

@Marcus Stokescan you start with a live-in flip or house hack instead?

I am from California, but lived in Peachtree City, Georgia last year (renting), and currently live in Germany as an Au Pair.

I buy and hold and do short term rentals and mid term rentals.Located in Racine Wisconsin  Hello Gabriel: I also live in Racine County there are some great deals our way and including southern milwaukee county too!   

Live in one side and renovate that side, then after the lease for the other unit is up move into that one and renovate it.

I used to live in Louisville KY and now I am in Tampa Florida. 

I've personally done just about every rehab scenario, properties I've lived in, properties bought as investments and even properties bought at auction.You've gotten good advice from folks on this list.