Can some of your concerns be mitigated (locally) through things like strong tenant vetting and property class selection?

I have sold some properties years ago on lease options where the tenant buyers actually exercise their right and purchased the property. ( I was in the deed.)The reason I am concerned to tie another person’s property up  with the lease option is that people can change their mind, as in the seller.  

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.

(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 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. 

Hey @Brandon LaRose, do you have the ability to use a Margin Loan against a taxable portfolio, or a policy loan against a permanent life policy?

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?