If you suggesting that winter is causing insurance to be higher, two things: the last years or see we call it brown grass season here in Milwaukee, because we don't get much snow anymore.

Had to find a replacement tenant right at the beginning of winter. 

Real estate overall is slower during winter than summer.

A common serious issue would be no heat in winter time.

Quote from @Ben Winter: Hi Yosef, I was truly inspired by your story.

Pros could be: Clean water + tub for each guest; on a well, so no water waste concern; can make it design-y + cute; can be used winter (hot water) + summer (cool water); goes better with forest location of the home than a traditional hot tub might; will hold same number of guests as hot tub would (2 people in each tub).In researching I have seen some people on Airbnb have these checked in amenities as 'hot tub', some 'private hot tub'.

We did a 10 day sail of the Exumas with friends this winter and I don't think I can ever vacation the same way again.

It's more work, but in the past, I had good experiences, especially with travel nurses, doctors and affluent out-of-state skiers renting for a whole month or winter.

Newer ones (2008+) are suffering from seasonality now but will pick it up in Q3-Q4: if you look at historical data, Miami Dade county has always had seasonality low volumes during summer time, due to hurricane season, holidays and less tourists visiting. 

A simple one page option saying. 1) I understand because of your circumstances you’d like to lease  MTM.2) I don’t usually do MTM leases and it’s harder to lease my property in the “winter”3) because you’ve been such good tenants I’d be willing to make an exception for you at the rate of $x+$200 with the stipulation your provide more at least a 31 day notice to give me time to find a new tenant.