I'm having my local ins co try to find a product that's closer to a traditional homeowners policy but still covers my bookings and at a decent price. 

We've found that HUD estimates tend to be low for repairs especially when considering what kind of quality you really want in the property.You need to factor in any potential CAPEX, maintenance, common area utilities, water & potential reserves (Reserves are really there to cover CAPEX items)

Traditional Finance is limiting thinking. 

That's very similar to offerings from Fundrise and RealtyMogul, though Rich Uncles has I believe the lowest minimum among those three.While they tout their low fees (3% vs. 7-10% in commissions for traditional PNLPs), there's are also a range of other fees outside of that 3% that investors should be aware of to be clear on how Rich Uncles in particular (and its affiliates) are compensated.

And I was trying to get a traditional loan where I was putting 20% down!!

I've learned to let a lot of questionable wear and tear items like carpet go.  

I would start out small by giving him routine odd jobs and do as you say, pay them on a per item basis right there on the spot.

If they refuse, I would send an itemized bill for the month rent due, deduct the security deposit, and return any interest.

There are also of course the traditional "fleshworld" sources of finding competent lenders:* Friend/family referrals that closed with a particular lender, esp those friends and family that we think have difficult or imperfect credit/income/asset situations. * Realtor referrals.

A few items that I need help with (having very little experience in construction):1) Estimating costs with a contractor who I've used before but not for a flipping deal.