Winter is slow.So if you picked up a couple of nice, used 4 season trailers, they could do OK IMHO.

I had my plane at Thermal for an entire winter and did a lot of the socal airports Catalina ( very cool) the most south I got I think was Borrego Springs..

It could have been deadly, but I never broke snap/leather.

For 20 years we have dealt with space heaters (of various types) for heating the room in the cold OH winters, or just ceiling fans for cooling in the summer.

Agreed - we may be looking back at this winter as a huge opportunity to scoop up before the market starts raging back up again

I have properties with swimming pool and playground so I am well aware of the risk management side but a winter item like this is a new for me! 

My goal is to have at least 5 rentals in the next 5 years, with the first rental being a new build house hack in Florida so that I can escape the Michigan winters and the Florida summers.

WINTER IS COMING.

And we do bigger trips during the winter.

If you have a multi-family property, then you have to figure out how to make the tenants share the responsibility or you hire someone to handle it for them.You have to consider insulation, maintenance of weather stripping on doors and windows, servicing the boiler/furnace, winterizing sprinkler systems, disconnecting garden hoses from hose bibs, and much more.It's very risky to manage rentals from a distance.