Trying to figure out a payment structure where he sees the fruits of our labor while also paying myself back.  

I also have developed a real interest in timber, and my background as an engineer lends this endeavor to be satisfying, intrinsically interesting, and I think the learning outcomes will be fruitful when taking the long view.On the flip-side of this, our primary real estate agent (for on market deals) has earned some credibility and trust from us in that he is NOT an investor, and has no intention of 'competing' with his customers (or even appearing as though he might be).I'm biased but I'd put the heaviest emphasis on the building/construction part of what you're laying out. 

Easier Fruit to pick so to speak.Good Luck!

Low hanging fruit, not a lot of experience needed.

Brandon was completely right when it comes to the fruitful conversations and massive knowledge available within current and previous threads. 

Manta.com can help you get the low hanging fruit on LLC ownership. 

Airbnb has continued to tweak their search algorithm, and new listings now get lots of juice in the first 3 months.

Don't get stuck on one property, run the numbers and make sure the juice is worth the squeeze. 

We own a primary residence that we just purchased so a heloc would not prove fruitful.

Get the low hanging fruit.