The monthly cost is kept low and is a workable system.

Actually, that extra 800 is post-addition of a bedroom I realize- its now a gross rent of about 6000, which I still think is workable.

If you have a fantastic relationship with a contractor, it might be workable, but other than that, that's going to be a big red flag to 99% of more buyers. 

I need to deep dive discuss with him without invading his privacy.Even if he cant finance, I'm wondering if there could still be a workable advantaged scenario here where I do get a loan, but we at least avoid 10K in realtor fees to get the price lower. 

Seems workable. 

Best recommendations for QUALITY of work, ability to work within the bid amount, ability to follow a schedule, honesty and character are the basis of any contract.  

IF homes were $200,000 and rents $2000, that would be workable, but that's not how it is.

Refinancing seems almost impossible and I'm getting really high rates and only ably 65% LTV options w a 670 score Is there a workable option that can let me access my equity in a way that allows me to grow my business?

Being as far north as you are self management would not be workable. 

Is this even workable?