I use Beyond pricing in my vacation rental markets and Pricelabs in my city/mid-term rental markets.

They may just vacate.

I am on vacation so I am a bit behind. 

My wife and I live in Chicago and vacation in San Diego every year.  

So if the homeowner saves energy or goes on a long vacation, they still get charged 100%.

They average 4-5 night stays, keep in mind im not in a vacation hot spot.

There are some New programs coming for 2025 for primary homes, Vacation homes, and investment properties.

It would cost less, initially, if a person kept it as four units and either rented the property out less of the time or not at all and kept it strictly as a vacation property.Any thoughts are appreciated

Ordinarily those tenant vacated damages would be too remote, but it sounds like they were contemplated by both parties at the time of contract.Were I in this situation I would be looking to state law to determine if the EMD is truly the extent of my potential liability as a buyer. 

No doubt; both of my neighbors at my vacation house got "free" roofs from guys who roam around after any storm and document that whatever storm damaged their roof - despite the fact they both had 15+ year old 3 tab asphalt shingles in the central Florida sun.