And if get real lucky, new siding, windows, garage doors to boot.

Windows painted shut 5.

I wouldn't limit it to roof as wind and water can damage other areas of the home..what if a window was left open and the interior now has water damage etc...Did you already bind your insurance (likely not if you are two weeks out) So there may not be a reason for them to dictate you get it reinspected. 

Where is everyone getting windows?

I signed up for the workshop also, but it's too late the cancel (3 business day window policy to cancel).

Also, with point 4 - is 18 months not a very short window to pay down the cost of a home?

With a small bench in there that the renter could slide in and out and sit on.

But given that the renovation was done such a long time ago, there are some wear and tear, like Window and HVAC, shower handle and stuff, so we have been updating those one thing at a time, and I'm hoping that this house can handle another 20 year so the $ we poured in for the new set of windows are worth it...Would appreciate any thoughts!

Get'r done @Tommy RayI think there can be some challenges to your power-point slide.  

If you cannot, get the tenants a couple of window AC units at $500 each, and tell them the central AC is broken and it is not possible to repair it at this time.