On the surface, it appears to be a straightforward role, but it becomes far more challenging when faced with issues like non-paying tenants requiring eviction or broken systems that haven't been properly followed.As a self-managing property owner, it is absolutely doable—but success depends on treating it like a business.

But I found an owner of a seafood company that had money but didn’t have time and I had time but didn’t have money.

Except that the owner cannot buy the property at auction!

How do they know if this is an owner stay that you blocked on your website, and it pushed over to Vrbo?

Trouble starts when owners “live off” the entity, instead of taking a salary or owner draw.  

Many companies charge lower initial fees which makes it easier to attract new owners but then charge inspection fees, after hours fees, fees for additional services etc.

@Nick Belsky gave you great advice.In this situation, best to keep it as simple as possible, and I often give two offers; first, perhaps an all cash (way below market) and let the owner know that it is what it is--a below-market offer.#2 would be the seller holds the financing--I wouldn't go to a 30-year amortization, especially with an 80-year-old seller. 

Charge them (not the owner) if it is something the tenant should be doing.

The hypothetical six months to find tenants might actually be 3 years, we don't know (if it was so easy to place tenants in that building, why haven't the current owners done exactly that?!).

Owner managed, but be identical name