(Respectfully- Please don't tell me to save up and quit my job it's just not realistic for me and won't be anytime soon)If you read the threads on BP concerning wholesaling, you should be able to draw a few conclusions1. 99% of people trying wholesaling fail2.

If it is someone you know you can give them a straight return as if its a loan - can provide a lower interest rate to provide upside - it really depends on the lender and what are they concerned with and what is their risk profile. 

I’m a little concerned about off season rentals.

If they do, you may have a chance under the scenario you're proposing - if they share your concern for it's condition (although that seems unlikely since they've been living with it the way it is for some time, it seems).If you own it, it's pretty lowbrow to expect a neighbor to invest in your property. 

Would a low enough sales price make all of my concerns go away?

Since the house is for sale, the most important concern is marketability.

Why even concern yourself with the legality if it’s self serving and harmful to your family member?  

You should have all the contracts readily at your disposal. having been an agent for 2 years already, it's really concerning that you wouldn't readily know the contracts for such as of yet, so I have to assume you have done exceptionally little the last 2 years. 

This type of policy is commonly used in new construction projects, fix-and-flip investments, or transactions where title concerns need to be addressed before completion.Early issue title insurance helps mitigate risks by ensuring that any unforeseen title issues do not delay or disrupt the transaction.

However, deferred maintenance is a key concern you need to keep front and center.