My background is in art and design, and I have enjoyed overseeing major renovation projects at each of our primary residences. 

Basically 1 loan with 2 houses in it.

If your statement is true, anyone doing work on their own house would be getting sued by their own insurance companies for weekend projects gone wrong.Sorry, not sure if I clarified anything on this or just muddied the waters more.  

My question is simple, are there fix/flip investors willing to fund and drive this type of a project for a % at closing? 

If you haven't done any projects yet, you're going to have to test the waters on the first one.  

I've noticed that roofing contractors in the area are pretty busy and they are pushing to get all their projects wrapped up before winter right now which can have an impact on price.  

This is obviously location and property specific, but we're working with partial numbers so far...let's assume you'd want to stay in the cabin on vacation:)  If we find a place for $300k with 25% down at 5% interest, conduct $50k of value-add rehab...renting it 12 weeks/year breaks the project even on a cash-flow basis incorporating all costs.  

Private investors perhaps- although they will want to see financials and earn interest in this "project".The tough part is in you wanting to hold the land for a year for appreciation.

Have you determined how you will be financing your projects? 

Currently, I am a project manager in Washington, DC looking to transition into flipping and managing my own properties within the next year.