And @Gail Kaitschuck I will be adding some supporting 4x4" posts and sistering the existing roof trusses with 2x6"'s, along with getting the roof done (stripped and re-shingled).  

@Stephen Kiser I built 10' ceilings and 9' ceilings, wood frame, wood floors 1st floor, carpet 2nd, granite tops, shaker cabinets, hardiboard siding, shingle roof, GE appliances.  

When we roll it into the C&D dumpsite, the guys hand-bombing shingles from the back of a pickup just stare and shake their heads :-)

And also the leaking roof will be fixed and re-shingled w/ style to match the property.

With it being only 2 years old(just replaced my roof this month with Class 4 Impact resistant shingles), do you think I can lower those "%'s" or should I keep them at 5%?

I am glad I was able to find that great price on the architectural shingles and my guys were able get it done quickly, I think it looks 100 times better than the 3 tab shingles and will increase the value even more. 

There may even be shortages of things like shingles adding to cost and time.

So for example I'm not going to buy my own shingles, gutters, siding, or drywall.

Next week, I want to look into gutter cleaning, also noticed that the back mansard roof is missing a section of slate shingles.

I had some storm damage from hurricane Irma at a property, really just a bunch of shingles broken.