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.  

I’m concerned about the economy.  

I have a few commercial bank contacts, but concerned they may just cut me out of the deal.

(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. 

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. 

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.

I’m a little concerned about off season rentals.

As a borrower shopping multiple lenders, your main concerns should be the following: 1.