Climate change was also a major contributor to the severity of the Louisiana floods last summer. 

My major issue is that the contractor issue seems like a chicken and egg situation.

I have 750+ credit score and no debts.

Is this something you recommend I look further into, or is there a major obstacle here that I'm missing? 

L.I write about No Bank No Credit financing.If you want to play in the sandbox of no money no credit, you need:Private Lenders (knowledge of self directed IRAs)JV Partners (splitting profits w cash partners)Creative Financing (sub2, land contracts, installment sales, TIC contracts, using notes, etc)I used to live in Mt Kisco, Westchester.I get what you are trying to do.Good luck!

They charged $39 for the measure that was credited towards the install.

Or should I require him to pay the deposit and maybe give a discount on monthly rent equal to amount of work done (monthly discount applied until amount is credited).

If you're credit is good it's likely a better option because there is no upfront mortgage insurance premium like there is for an FHA loan.

It is clean and safe, but not overly nice, and there is a major eyesore property next door to this one.It has new siding, new paint and new floors and does not appear to have super aged water heater/ac/roof but I intend to have a home inspection to verify the big stuff.

Do the credit check.