I’m in the same boat with working, investing, and juggling all this with raising 2.5 year old!

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. 

It sounds like the tenant has solid evidence their check or auto payment was received by the wrong party.  

Make sure both parties fully understand and agree on:How profits/losses will be split Who is responsible for what (e.g., repairs, management, communication with the seller).Exit strategies in case things don’t go as planned.When you do find the right partner make sure to create a joint venture agreement that outlines all of this clearly.

Hey @Beau Wollens, late to the party, but curious to know what you ended up doing here.

Now that is taken care of; time to address the renter's insurance.As mentioned by someone above, you can be listed on the policy as insured or interested party.  

@Spencer Cornelia can't believe i missed this part. i was actually browsing youtube and came across your channel, small world!

Challenge: It's in a neighborhood (no HOA), and renting the entire property (sleeps 25 in total) caused problems in the neighborhood, due to noise and parties – so we only rent the separate cabins now.

Part 2 of 3 - In Subject-to deals, can BOTH parties deduct the interest?

Hopefully you can state simply (and truthfully)  at the end of the showing that you have other interested parties to whom you are showing the property and will let them know in due course.