Seems like okaloosa is very busy and lucrative during summer, but kind of a dead town in the winter. 

You also have to deal with winter weather in the northern states and possibility of pipes freezing and higher heat costs (which would be paid by the tenant once rented out).

Inspector couldnt test it out due to it being winter.

Vacant properties in the winter run the risk of pipes bursting so avoid those.

I have a wooden retention wall as attached which is about 30 year old I think from the time when this building was constructed, I have made slope down on right hand side corner last year for landscapers, tenants to go into ditch to cut the grass rather than leave it become mini forest with poison ivy plants as well there.

I can also see winter break being a time that families may use to look for houses, if they are looking to move.

Chicago winters can be harsh, so we're curious if anyone has had a good experience using a heat pump with an ancillary heat strip for those extremely cold days when the heat pump can't keep up.

The home prices are also much more affordable, and from what I am learning, the Salt Lake City market is getting very hot, especially considering the Salt Lake City Winter Olympics in 2034. 

I plan to invest in one of their Ohio properties this fall/winter. 

Sam,I found that doing the 1031 exchanges during the winter has worked well for me.