I found a licensed GC and started giving him small jobs, first the exterior paint, then the interior paint, then I just had him finish the job as he did good fast work for me.

You want to keep up the interior and exterior as pristine as you would expect a Hilton Hotel to be, while maintaining an aura of a friendly home.Being cheap is a sure way to failure. 

My wife has an amazing eye in regards to interior design (Her day job). 

I read that scuppers are easier to maintain and are a cheaper way to drain flat roofs versus gutters or interior drains.  

Do it now , because when there IS a problem with the roof leaking , all the contractors will be busy and you will be adding interior repairs to your list 

It looks like a modern-ish interior design, but that's not going to help with the morning commuter who just wants to zoom through your drive-through and get back on the road. 

She is in terrible health and the interior of the home is in terrible shape/living condition.

Originally posted by @Chris Connolly:I believe you are able to do the repairs yourself, if you're hiring someone, they might have to be certified (or that's only when you KNOW that there's lead paint, ie having it tested or it show up in the disclosure) "The law requires contractors to get certified in lead-safe work practices if their work disturbs more than 6 square feet of paint on the interior or a 20-square-foot section on the exterior of a home built before 1978." 

I was thinking an exterior door (it's an interior staircase) for security, is that a possibility or a bad idea?

Definitely needs new flooring, total interior paint job, probably new appliances.