I will be living next door in another house (our new house) and can manage the rental full time.I live in a seasonal vacation area with a military base nearby.

I would say Private LenderHard money and a Heloc would work but i don't know how much seasoning you need.   

Exclusions are Acts of God, insured perils, weather days need to be assessed to the season, lag time of suppliers or materials delayed or not delivered, delays caused by inspectors or regulatory matters beyond the control of the contractor, defective materials and/or equipment installed in the project, normal amounts of waste and other matters depending on the project.About all you can hold a contractor's feet to the fire on, is failure to continue work when work can be accomplished, their mistakes that exceed some agreed cut off (you will have mistakes and waste) worker's conduct or failure to show, work not to workman like standards or torts, such as walking off the job.

@James Wise I think that this exercise you are attempting is totally wasted on the active, seasoned BP member as they have been down the road and worked hard to find their niche and make it work for them.  

While I don't operate in those temps we have a definite moving season and with aggressive marketing it is doable!

It's great to have a seasoned investor join our ranks.

Now that I have enough equity & seasoned I am able to refinance.Closing costs $2200.00 each.

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.