I could see in NJ where you would want to because the winter time is dead.

Now that I own rentals my debt cycles with winter fuel and sometimes remodels being put on a credit card.

We found Michigan winters to be blah and too long/drawn out.

It could be heat in the winter(in Michigan) or AC in the summer (imagine them running AC at 70 degrees all summer in Phoenix) or just general disregard for leaving lights on and things like that.

Dead winter is not an ideal time to rent out a property so I expect it could take me 4-6 weeks or require discounting.

Quote from @Marc Winter: Based on the last 4 housing crashes I've survived (and lived to talk about), we are teetering on the brink of a major downturn in many geographic areas.  

Haven't seen activity increase like crazy but I think end of August(after school starts) activity will increase before the Winter

In Pinehurst NC, known for golf and the US Open, we do have some STR that are often medium term...during the winter months when golf is not as enjoyable, we get medium term renters. 

It is undoubtedly one of the best cities in the world.... especially before winter lol. 

For example crank the heat up to 85 degrees and open all the windows in winter causing a $1,000 heating bill for the month!