Tenant claims they were not like this when he moved in (I bought this house with these tenants in place a few years ago, so I never saw the house without stuff in it until they moved out)  For all I know they swell and buckle in the summer and sit flat in the winter. 

My girlfriend and I are interested in buying into the upper Michigan STR markets (Traverse City, Charlevoix, Petoskey, Bay Harbor, etc), hoping we can take advantage of the hot vacation rental market up there in the summers and the popular ski slopes for the winters. 

Recent winter months was the first time we have experienced typical seasonal slowdown since Covid. 

Ideally, I would STR it to either the wedding hall or seasonally, although the purpose of snow-birding is to be in CT in the summers (wedding season) and Florida for the winters.

We proceeded to have the power turned on for our de-winterization and the plumber on hand for this and thats when we saw the dilemma under the house, copper plumbing gone, electrical wiring gone.

Often, properties priced at peak season rates can have very low occupancy during the winter.

I had such a great time last winter riding an adventure bike (motorcycle) all the way down to the southern tip last winter (which is summer there) that we want to go back and spend some time in Chile and Argentina this winter.

Quote from @Tom Winter: I'm currently house hacking (renting rooms) my current primary residence which is a single family home and has a mortgage.

This is an unexpected expense on top of a complete renovation plan for the winter.

Also, expectedly, inventory during winter months is significantly lower. ($575/night for a newer 3 bedroom mid December)