To fund additional investments, consider side income, creative financing or creating a timeline with your co-owner for converting property B into a rental to generate cash flow.

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.  

@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. 

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.

Heck go to the casino and put it on roulette wheel of black or red. 

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

Owner managed, but be identical name

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?!).