I want to keep him enticed/rewarded enough to stay involved down the line but want to make sure I don't over-promise and stall my future plans. 

RailRoad which runs the childrens train the "Polar Express" through the end of the year and keeps town very busy with some 70k plus visitors.I would echo most of what Amy had to say about the biggest factors to consider for a mountain rental would be  accesability, view, hot tub, fire pits and lastly we have seen a shift from people wanting to be remote to being closer to town.  

If you want to work in the business get some sales training (find the job with the best sales training that you can land).

Hello EveryoneI'm Real ABR, GRI Estate Agent in San Antonio Texas, I mentor new real estate agents and investors to train them the whole prosses and TREC rules.

I am in fact looking at bringing a "note buying/selling" training program to Lexington, in Nov.  

An executive of a business authorized to sign such documents is often an employee, not necessarily an owner.If bankers won't let you sign like that, take your better attorney along and have him/her explain it to them.I have one who even trains IRS agents on the proper interpretation of the tax code (he, his partners and staff consistently win audits).

Honestly, I would start by finding the highest rated training you can get into.

The first couple of flips will be training grounds for us and will not be part of the show.

Like @Bill S. mentioned there is an awesome REI Club here in GJ, check out this BP link for contact info: https://www.biggerpockets.com/rei/colorado-real-estate-investment-clubs/There are some fantastic training events coming up this month at wCAREi on Foreclosure Investing (yes, you can wholesale foreclosures!)

People with this train of thought shock me.