So how do seasoned investors decide what is the best way to deploy cash?

I can't speak on whether or not your idea is a good investment or not since everyone has their own goals and it sounds like you just want a place you can use often and not worried about the monetary return.With prices in the Vail area and the fact that it would be tough to fill up during the "off season," the chances of generating positive cash flow are fairly slim.  

@Larry Russell I would look for smaller regional banks or credit unions for better seasoning expectations. 

Unless I missed it, did you first confirm that there is a boatload of equity and profit potential, especially allowing for repairs of a house that been vacant through a number of harsh seasons?

It means a lot coming from a seasoned investor such as yourself.

Exceptions to this would include scenarios where the investors are willing to work you through mistakes (i.e. they aren't Uncle Joe, they are seasoned investors that will walk you through difficult projects) and scenarios where the truly great deal is simply out of your reach alone.But, for most people, I bet that getting started small, on your own, with 100% ownership is probably ideal. 

I live frugally and have travelled all over the country doing seasonal marine bio gigs, eventually leading me from Charleston, SC to the Dominican Republic to now, Alaska.  

They can afford to do this because of 1 and 3 in the list above...and they try to get some of 2 too.Type 2: Local seasoned investors.

I am working on a few deals with another BP member buying some fix and flips I am going to fund and the escrow function is coming from India.. 17 e mails a day 4 to 5 calls wanting me to fund without proper docs and or title commitments.My on the ground partner is ON it totally so we don't have a problem as he is an expert in his market and a RE broker and very seasoned so he won't let anything slip by.. but it this were Escrow functions are going off shore.. incredible.

Swim, ski, bike, ride, foliage.We don't have the year round properties that offer one season.