Some thoughts on your situation overall:In terms of vetting, I personally there is a limit to how much you can mitigate risks when working with a smaller contractor.

Its money well spent land development is high risk high reward.. depending on Jurisdiction. 

It's all about risk in the event of a lawsuit, which can also usually be covered by insurance.- If you decide to have an LLC for each property, creating a Management LLC that all the other LLCs "hire" to run their books, will allow you to only require a bank accont for the Management LLC.2) You may not be able to do a Trust.

You will pay for the higher risk with higher rates and origination fees but if the deal makes sense then congrats.

In a stable free economy the natural tendency is for prices to go down not up.

At the risk of taking flak here, I'm going to say I've seen a lot of super cute stock tank pools that are low-cost options. 

Although I’m just getting started, luckily I've being able to invest in 2 mutli-family properties in New Jersey, it was a lot of work but I really enjoyed it.

And lowest risk. 

Have you considered a cash-out refi instead of a HELOC to lock in a fixed rate and avoid variable rate risks?

Feel free to PM me.