How do you all mitigate these risks?   

This is a great place to learn and to connect with people so take advantage of all the great resources.Welcome aboard and best of luck investing!

Based on all those factors, your best chance would be to partner with a more seasoned investor to get loans.

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

All my HOAs require licensed and bonded workers.

I get get really good prices for home games, graduation, ceremonies, moving kids in and out etc.I get all these bookings from VRBO.

I won't go into all the details, but there always ends up being a significant problem in the documents I get or don't get, in negotiations, etc, and the trigger never gets pulled.For a variety reasons in addition to the above, including my wife's encouragement, I've decided to take a serious look at going the real estate route instead.

Is it as simple as getting the site designed and engineered for the footprint, cleared and graded (all of which I am comfortable with), and then hiring a GC to build the building?

Update: Decided to go with Total Quality Lending and all is going well so far.  

Soft close on all cabinetry (think thats probably pretty standard in most areas now), dimmers on all light switches, mood lighting in kitchen, and cased windows rather than drywall returns.