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.

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?!).

I’m just trying to play it as safe as possible considering it’s been vacant for so long and I have no idea the condition in which the previous owner left things.  

Yo Omari...how will your letter be worded toward the homes owners?

I imagine owners can live there, you just can't rent it.