The proper answer is "it depends" I don't know anything about your case.I do prefer simple over unnecessary complexity.

Make the offer appealing by highlighting the short-term ROI from his renovation expertise and potential profit-sharing during the partnership.

Maybe...In human terms?

His reason was the only thing he knew to do with the proceeds was to loan it back out at 12%, and he would be "behind" where he is now in cashflow.His proceeds would have given him options up to and including PE, but he is a simple man and in his case holding was the option for now. 

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

I'm passionate about creating secure, long-term housing solutions that balance tenant stability with strong returns.

That is one of my moves is to report Baselane to FTC for such fradulent practices, despite covered in footnotes in terms and conditions.

It's simple but not always easy. 

But, if steady long term cashflow is a goal, with no management, one can always sell farm land on a low down private contract.

Please reach out and I can let you know the terms to hang your license with me.