I am no expert on Florida or Winter Springs, so I cannot give you specific advice on what to adjust for in your area without spending time learning that area.

My thoughts are to get them on a 6 month lease in Nov. at $1100/mo, and then start an annual lease In June, whIch Is a more favorable tIme to fInd tenants vs. the wInter In MN.

Coming up to the winter months I'm nervous it'll only become harder to find someone!

There are also smaller college towns like mcminnville and forest grove that might get you a lower entry point, but put you a ways from Portland

the one disadvantage of month to month is if the tenant decides to move out in the winter slow months.

Usually once a house is abandoned and in foreclosure, a preservation company applies the orange stickers saying this house has been winterized or has lock changes, etc.

Rents stable around $1,000 and homes at or below $100k.(6) Forest Park (1263 Watts Rd you showed us) Decent neighborhood, didn't get a chance to drive around too much.Rents around $1,000 and homes at or below $100k.(7) College Park Didn't drive too much of, rents looked strong and saw some more expensive pockets there.

These are typically more like corporate housing or traveling medical professionals.Short term rentals—We've used Airbnb selectively as a way to turbo-charge properties that maybe have a small funky unit that can't command strong rents but still is a bear to heat in the winter. 

Large house = $1,500/mo ($900 for 3 bed, $600 for 2 bed)Small house = $1,100/mo ($550 for each unit)I see a huge opportunity here to buy these houses this fall/winter and let the current leases expire and then rehab them next spring/summer just in time to rent to nurses/young professionals working at the hospital.

Especially as we go into a winter session where sales start to slow down and purchase prices decrease.