Once you have a property under contract have it inspected to determine the current condition and life expectancy of all major components and appliances.  

Life is unpredictable and unexpected repairs/vacancies could really stir some chaos if you try to buy when not ready.P.s.

Next property was an unexpected $5,500 for a furnace and duct work.

If you get a quote on the roof and the comps support your purchase price + the repairs with a little bit more wiggle room in the budget for an unexpected repair or expense then your deal is likely a good start.

You are already at the top of your budget, even if the seller agree to reduce the price, do you have budget for unexpected stuff you find during your repair?  

Finally, expect the unexpected. 

Obviously many costs are unexpected and can be difficult to quantify. 

He is willing to work with me as we learn it all together. he wants it to be a win-win, so once we get this one done, we can just move on to the next.There are a couple people who mentioned refis without a DTI component, and I am intrigued by that moving forward as well.

Or a significant expense unexpectedly pops up (it will happen).

Or...other recommendations on how we could finance the projects and some component of the "fix"?