As my first project I would like to purchase the property out of the trust, maybe move into my newly formed LLC, and convert to a 2 family.

Like you I think I made my first investment in a true syndication when I was in my early 60s. the sponsor is what matters.. asset OK  but if the sponsor is not top notch I dont care how good the project is..

I have many years of construction experience and have also done a fix and flip, in addition to ground up construction, as well as 10 years of entrepreneurial experience running a paddle board rental company, and advancing science through developing theoretical methods for efficient large scale simulations...I guess my problem is I can't seem to figure out how to find the money to do more projects, which is why I've been trying to sell my house.

I have borrowed against the property to fund other development projects via a heloc.

A smarter approach would involve thorough market research, realistic projections on occupancy rates, and understanding that not every location is still a goldmine for STRs.

I also know that if I manage the project well, it will come in near the original estimate and at worst between the original and the high estimate.

This takes perhaps a few projects to get the hang of. 

Where are these treehouse projects located?

I see this a lot, and I think there's been so many bad projection tools on the market that the "what did this house earn" is a valid question.For investment properties there is a true number and buyers want to know how that compares to the projections. 

I’ve used Asana for managing day-to-day tasks and projects, and it’s been a huge help in keeping everything organized.