I lived in Bozeman, Montana, a resort town with a minimum home price in the 250s.

You need to find lenders that are self funding and not relying on money from the few major capital players that most of the lenders in that space get their funding from.

I'm looking into places similar Windsor Hills resorts where short term rentals are allowed and were actually built for the short term market. 

@John Morgan Do you have a nightly rental through a local resort in Branson?

It's been my understanding that hard money loans are "last resort" options due to their higher rates and potential for recourse.

. :) You could plan out the whole resort, but start with one and see how it goes.

Near the ski resorts will cost millions with gross revenue in the 5 figures. 

As long as you really nail down the criteria of what your looking for you should be able to build fairly rapidly, and a lot of the values that made you a successful soccer player will transfer nicely over to real estate.  

context absolutely matters. if you want a handyman to come over and install a few cabinets, you can probably take on his risk. if you have someone install a roof, you're crazy to take that liability on yourself. you want to use your insurance as a last resort in every scenario, so having the person doing the work covering their own liability is really important. for small stuff when you're new you can skirt around this to create margins a bit, but as you get bigger you want to go more legit and worry more about reducing potential downsides. 

As you keep playing you start to hone your swing and you become a better player with consistency.