Disallowed losses under wash sale rules increase the cost basis of replacement securities, potentially reducing future taxable gains.This post does not create a CPA-Client relationship.

I'm hesitant to set a utility cap, as I worry that disclosing a specific amount (like $500) could deter potential tenants.

If so, do you have any paperwork that supports the vesting to be able to show a potential lender? 

The other potential problem is the term of the proposed renter not sure exactly we are going to deal with their lease when it comes time to sell.  

Maybe that's not "illegal" but it is potentially actionable.

Sounds like a good plan, should have plenty of options available.I would be cognizant of any group you talk with on two areas, the location of the property including any potential concerns of it being 'rural', as well as the minimum purchase price and/or minimum loan amounts.

Each potential buyer has come to their own conclusion that it would be too much hassle and risk to manage in this fashion vs a traditional rental even though the average cap rate in our area has been half that at best.

BRRRR with a bang: If you can pull this off, the value-add potential is huge.

$500k would be enough to go out and buy something else leveraged that would potentially get you a better return.

You are best off to raise the rent and give the tenant the option to stay.Also, I hear a lot on here that "rents should be", "the potential rents are"... make sure that you do your due diligence when calculating potential rents because most new owner OVER estimate them.