I have been editing it based on a state-specific lease template which contains 15 pages.

https://www.biggerpockets.com/users/ZacharyCole/referenceshttps://www.biggerpockets.com/forums/92/topics/518583-feedback-on-renttoretirement-and-zach-lemasterhttps://www.biggerpockets.com/forums/92/topics/765347-rent-to-retirement-reviewhttps://www.biggerpockets.com/forums/850/topics/895660-my-first-investment-property-an-out-of-state-dealhttps://www.biggerpockets.com/co/RentToRetirementhttps://www.biggerpockets.com/forums/92/topics/929410-rent-to-retirement-updates?

Your state and local law may have some mandates that you must follow regarding treatment of those funds.

I self managed and I live out of state. 

I’m going out there soon to get a feel for the state.

If I was your brother getting my REI portfolio started, is there any advice, strategies, links, literature, articles, or people to follow that you would recommend for someone extremely leery of financial risk?

Also the added value from developing the lot is more in the vacant part than in the already built portion.If we do have to sell the whole parcel, another option could be a performance bond and a lien on the property.Looking up pros and cons of performance bonds, this interesting article comes uphttps://www.lauriebrennan.com/blog/to-bond-or-not-to-bond-th... 

The reason being that the State has allowed the four counties to regulate STRs, and why each county does it differently.

If yes, then maybe consider a PM software like Hemlane, which will give you access to leases from different states and rocket lawyer.

A co-host will be expected to know this and how to achieve it and execute on it in order to be successful.Also, keep in mind some states are very strict about what it means to be a co-host.