Hey Rob, if my client or myself was in a similar situation my advice to myself and my client  would be... if the profit margins are there, you have the capital to make the deal happen, there's news everywhere about rates being cut in the near future, and it doesn't put your family in any major financial stress by you making this deal happen and more importantly your comfortable!

partner with a RE attorney in your state, and get a PM company for the future

I think you're on the right track, a net-zero living expense is awesome and will do a lot for your future investing endeavors.

However, he is concerned about what might happen to the property in the future once I am gone.

You will have to make some estimations about future growth as any underwriter does. 

Or if they want a high interest rate, and your numbers will not work at that interest rate, or if they really want a crazy high price where it will be difficult to cash flow and refinance in the future.

You can't just throw up any old short-term rental here and expect to succeed anymore.

By focusing on strategic locations, sustainability, and market demand, investors can leverage new construction to secure their financial future—just as Buffett does.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

. - whatever a contractor says, expect double lol