I once rented a 5bed/3bath in two days, just a week before Christmas when the ground was covered with snow and ice.Sitting vacant in the winter increases the risk of frozen pipes or other expensive problems.

It is the Winter time so it's a slower time but I think you are overpriced.

It's not fun dealing with aging parents.

I would keep them at least until the summer because it is not great to lease in the winter. 

Easier to do with a duplex year by year, but when I rented to students I would quickly renovate for winter break. 

Sometimes HOA’s can be fun to deal with though on the other side. 

RehabbingIt was heading into winter and we had three deals that were not moving, Nathan couldn’t find investors to buy them from us.

I work more hours than I ever did as a W2 employee, but it's FUN.

In addition, I am considering changing my furnaces/boilers to have plug-in cords instead of being hard wired so that if there is a power outage in winter that I could power that heating system with a portable power station.

Winter time is rough for renting especially in states like IL with rougher winters.