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. 

@Mark Forest It's true that Detroit is not great for buy and hold appreciation.

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

Interested in South East Raleigh, North Raleigh and Wake Forest. 

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.

My understanding is as follow for (but I remember reading about some very narrow exceptions that may be different), as long as the policy does not become a MEC.premium are not deductible (after tax).grow of the cash value is tax deferredWithdrawals from cash value are taxable above the premium basis (FIFO).Death benefit to a beneficiary are tax free but are counted towards the total estate value for estate tax.

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.

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.

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.