One thing I'll say regarding your reference to a "strong Airbnb history" is past performance is no guarantee of future results.

I've had 2 issues with tenants not paying rent resulting in them leaving and yes they left a mess, but we cleaned it up, got it re-rented (for a lot more money as there are rent caps in place in that area) and moved on.My first rental was accidental-I bought it to live in and moved and converted it into a rental. 

I know the basics  about RE but i'm eager to learn more and grow within the community.

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

Generally - seasoning concerns are at the very most 12 months - if bought over a year ago, nothing to really worry about with any lender re: seasoning

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

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

I'd get an addendum in writing with the seller that states this. 

@J ScottThanks taking the time to write to my post.