I guess make sure the places have been winterized or the utilities have been left on, if they've been left on and you have any homeless I would assume squatters.

@John Collins2 months, at this time last winter.

Part of the difficulty in getting a solid answer on this question is it’s winter in Minnesota and the land is frozen and covered in snow.

In our own home, a single fam, we would walk around in sweats during the winter and be comfortable doing so. 

I will look into my specific fear to see how to overcome or use it, I have a long road ahead of me,  I want to get my first house hack property in the winter of 2020!!!

I'd say the North Dallas home was a lot easier to rent out, I had one month of vacancy on my Irving home for 1 room, which wasn't terrible as I purchased during winter season.

Thank you all in advance and have a great winter,Eli

Flip side of the argument Its easy for them not to pay the gas bill, but at least there are laws about locking gas meters in the dead of winter here.Make sure the oil tank is not buried underground.

I'm considering selling it, and the land is worth about $50,000-60k (located in forest park).Currently, there are 5 spots lined next to eachother on the short end of the property which crosses the two 25' x 125' lots.

One thing I would highly recommend for your first purchase is to buy in the winter months, preferably December/ Xmas New Years time.