You state that everything is equal but are concerned that not everything is equal...It's very possible to see a price spread like that even with comparable coverage but it's also vitally important you work with someone that has your back to make sure you understand your coverage before you'd have to use it.  

You might explore partnerships where you fund all-cash deals in exchange for a portion of the profit.

We financed this deal using a conventional loan, and taking portions of my 401K out to make the down payment and stage the house for STR and MTR.

Partial 1031 Exchange: If you back out of the condo deal, you can still defer taxes on the portion already reinvested (the vacation rental) and pay capital gains tax only on the unused portion ("boot").3.

In those cases, if the HOA assessment is a direct result of the insured loss, it can kick in a specified amount towards the individual HOA members portion of the assessment.  

Make sure the lender gives you what is called "Non-Dutch Interest" on the rehab portion, that means you do not pay interest on the rehab funds until you use them.

So they can do a 1031 only on their portion. 

Most likely insurance is going to want the whole house not a shared portion of it.

Out of curisosity, are you considering utility reimbursement portion as "Owner making money?" 

If it doesn't then I would give the previous owner their portion.