The one thing I do not like is that you cannot serve him personally which is for me the biggest hurdle.

I’ve always believed that if the lender is a “partner” sharing exposure and not an at cost money provider dividing the profit of the deal into three sections is appropriate   MoneyMarketingManagement This said it’s not unreasonable to allow a minimum return after “X” profit.  

That rarely happens and is an unreasonable expectation.

.- A hurdle here is that your loan amount drops below $100k, which is the minimum for many lenders.

You don't know the law, you don't know how to handle difficult tenants, and you aren't local to work on it.This is what Ohio law says: “The tenant shall not unreasonably withhold consent for the landlord to enter into the dwelling unit in order to inspect the premises, make ordinary, necessary, or agreed repairs, decorations, alterations, or improvements, deliver parcels that are too large for the tenant’s mail facilities, supply necessary or agreed services, or exhibit the dwelling unit to prospective or actual purchasers, mortgagees, tenants, workmen, or contractors.”I would give the tenant a short, direct warning that they have 72 hours to coordinate with the vendor and set a schedule for repairs.

And is there any angle I'm not considering that would make this an unreasonable idea to pursue?

Your biggest hurdle will be dealing with regulation red tape, and finding a place where it can be done.

I do t what to argue the merits of the importance of title searching for title insurance I get it you love them you want to marry them they saved you money unhappy for you I have my opinion you have yours I'm just saying would you take a step back and you look at the amount of BS that they throw in there with what they're doing and the fact that they do forget who works for who it's crazy that being said I'm just wondering how long this is going to go on for every time the house sells and if you do have some of that doesn't want to sign off as is their right not to want to give off all the information especially in the climate of fraud that you talked about is there a solutionNo where in your screed did you give an explanation for why you didn't get a title policy when you bought the property from your friend, all you did was complain that the title company is being unreasonable and uncaring by refusing to help you clear up a problem of your own making. 

DTI had become my hurdle, making regular plain vanilla mortgages difficult.

it might help to be able to point to your real estate agent as the unreasonable person who won't let close without resolving the issue.