We installed an oversized pool heater at one of our own FL properties and it is a huuuuge draw in the winter!!!!

This is extremely troublesome during the hard Colorado winter weather.

I'm also moving to the MTR strategy as we go to the fall/winter seasons here in Denver. 4 months out of the year it's reeeaaal slow as an STR, but MTR strat could keep things more afloat.Cheers,Ian

As I mentioned in my original post on here, the warmer summer months will take care of themselves, but if you want to have the STR operating all year round, the winter months require much more effort to make your property a place people will want to visit and stay even when the weather gets nasty.Nothing against VRBO, but I would also take a few minutes to check out what listings are available on Airbnb as well. 

Maybe a PB court in the summer and a hot tub on the court in the winter? 

Depending on where it is, I might work with Section 8 housing in my town (Winter Haven) or set up STRs in the other 3.

If you're able to invest in a market where people usually go for vacation in the winter like FL, AZ, Carolinas potentially, then you can get something soon and immediately be renting it and getting a return on your investment this fall.

Rentals for 30 days or longer you don’t need a permit, ski leases are a great option if you don’t plan to use the place at all in the winter. 

Heating costs go up in winter, as does electricity due to the reduced natural light and more people indoors.

Let’s just say as we head to Mexico for two months this winter, he has no regrets of finally doing it… lol Our current situation (studio in back yard) is the most lucrative I’ve ever done and the property has appreciated nicely in the five years we have owned it.