Also, winter season in general (in VA) tends to be more difficult than renting in spring and summer months for me.

(more time, not included above) The time of year is also important, in the winter i'm looking at $40-70 a night and in the summer i'm looking at $99-$150 a night.

I tried a longer short-term rental over Winter season and got a lot of interest and ended up with an excellent corporate emplumas whose employer paid me directly!

They have a job loss, or are being transferred or have bought a second house and can't afford both, or are in a divorce, or have inherited a house and can't make the payments or are downsizing or are upsizing or are going into assisted living or have been given a new military assignment, or own a house and have gotten married and don't need two houses or are a burned out landlord (they tried "Buy & Hold" and they don't like that type of investment) or they don't like the heat in the summer and want to move or they don't like the cold in the winter and want to move or they miss their family "back home" and it goes on and on.

Orygun winters done with those3.

This past winter, I investigated the possibility of a beach property to be thru AirBNB or VRBO in The Florida panhandle (especially Panama City) or Myrtle Beach, SC, etc.  

Other activities like skiing, snowboarding, and a Golf Course for Winter and Summer outings are also contained within the Casino plan. 

If you're in the North/North East, hold it for one winter before purchasing another.  

Absentee owners of FL condos are most likely retirees who come visit in the winter... 

Relocating to Apopka/Winter Garden/Clermont in 2 weeks.