I have two offers on my property coming in, and was wondering if people have experiences (good or bad) with the banks that would provide the mortgage to these buyers.

Both are pre-approved.  Buyer #1 will get their mortgage with US Bank.  Buyer #2 is using a mortgage broker and going through a lesser traditional type of lender.  Buyer #2 needed to go this route because their traditional bank wouldn't pre-approve them for quite enough (though their income doubled in 2017 from 2016) because they haven't filed their tax return yet for 2017 (obviously).

We own a rural property, which has all the things banks can give you a hard time for (well, septic, mnfd home, etc.).  Since Buyer #2 is going with a less traditional lender that is more lenient with their self-employed status, my theory is that perhaps they will be also more lenient with the whole underwriting process.  Has anyone found this to be true?  Also, how do people experience the underwriting process with US Bank?

Obviously there's no guarantees, but I'm just wondering with all things being equal, what might be the best shot for a successful closing with the least amount of pain.