Even though your Realtor might be good and helpful their ultimate goal is to get the house sold and no one will see the vision you have set for yourself, in the same light that you will.

@James Carlson You probably already know my thoughts on STRs vis a vis 'affordable housing' :-)But this is going to play out as it will, and ultimately even Gov't intervention/restriction will fall to the power of the free market, so we'll see how it goes.I wish the property owners and entrepreneurs well, although some of them will learn that 'elections have consequences' as 44 so famously said.

Ultimately, it’s about what aligns with your budget, risk tolerance, and long-term plans.

But in the Op's case, the partner doesn't have a say which leads to upset partners, litigation and ultimately to failed investments. 

I would lean towards recommending that you pursue the deal - plus having the property remain in your family may be a net positive for you and your extended family regardless of the ultimate financial return. 

I’ve also seen success with titles that create an emotional connection—something like, ‘Ultimate Family Escape with Stunning Views!’

. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

My goal is to gain a solid understanding of the process, master deal analysis, and ultimately close my first deal.Right now, I’m focused on learning the basics — from finding motivated sellers to building a strong network of cash buyers.

Many times I would take an aggressive stance on certain deductions and wanted to clear them with him as he ultimately signed off on the return.

If you end up in Ohio and you end up in Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods.