So is this just as simple as showing how much the property makes or do they also look at personal debt to income, credit score, reserves etc as well.

(Either with the roofing company, a heloc, or a personal loan.)Either way you will probably be way ahead on interest saved unless you have a sub 6% interest rate.

However, a common benchmark is aiming for at least 6-8% cash-on-cash return based on your total investment (purchase price + rehab + closing costs).Always factor in appreciation potential, tax benefits, and personal risk tolerance.

My recommendation would be to engage an investment property focused realtor (not a general residential realtor) and let that person guide you through the process from pre-qualification to market/property valuation and selection. 

Talk with the syndicate/Reit and your tax person. 

I've personally sold a number of properties to VA buyers.

If you need a conntection in Upstate NY I can direct you to the right person.

I personally would fix the 3 windows and maybe consider cutting the rent a little more to gather more interest. 

Remember that for most owners, their business is very personal to them.

I have two phones, one for business and one for personal.