I'm trying to figure out where my current knowledge would best fit for now while I learn new things.

In a partnership I'm involved in where I brought the deal and will be handling day to day decision making and managing the original renovation we are splitting things 65-35 so the partner bringing the funds will make around a 15% coc return annually.

I'm sure you will fit right in coming from Vail. 

I would think the involvement of any such association could be a hindrance to running a legal short term rental since so many restrict them. 

So far, I've started working with a real estate agent I think is great, and also believe I've identified a property manager that I think is a good fit for me.The agent has been bringing me deals that seem to fit my parameters.

There are some potential pit falls with that plan (mainly there's a chance that 5% isn't enough to match the work involved w/ X number of doors.

Get involved and meet some people.

I don't use the license at all now, and being an agent never fit my lifestyle.

Is a 20yr mortgage the best fit for your goals?  

Maybe that would give me a better idea as to who you might be a good fit with.