There were some other good points brought up here as why he may not want or be able to enter into a fiduciary relationship however his answer would make me scratch my head and based off what you know now ask him more about those things people here have brought up. 

Depending on how much liquid funds you have available, you could always get started with a Hard Money Lender, just be aware of all the costs associated with the lender and be sure to include in your analysis of the property.

This is harder to do if you're 50 and have kids headed for college. 

Any good HML will know this number off the top of their head.

Now I am headed south to the warmer climate to semi-retire.Here is my QUESTION?

If truly all it needs is a new roof to be complete and ready to sell then a few ideas off the top of my head could be:1)  Borrow the money from friends or family to replace the roof2)  Put the cost of the roof on a no/low interest credit card and pay it off as soon as the house sells3)  Go through a home improvement store (like Home Depot) that offers financing for larger projects like roof replacement4)  Don't replace the roof and just lower your sales price or offer the buyers a credit to fix it themselves after closing

Height of a detached accessory dwelling unit shall not exceed the height of the associated primary dwelling unit.

My wife and I are fairly new to real estate investing, but are looking to dive into it head on (which I’m guessing is the same as prettt much everyone on this site).

You should check out the Chicago Creative Investors Association run by Jane Garvey.

I worked in the medical field for close to ten years before deciding to jump ship and dive head first into REI.