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.

We actually couldn't get at certain areas to assess the actual damage done by the wisteria that hadn't been pruned in at least 4 years but it was getting behind trim and under the roof shingles up high as an example.

There were shingles, wood, and shingles on top of each other.

He did say it was missing shingles, which it was not last year when we had it checked.

Roof is original (Shingle) $4k is as I expect to have to put in about $1k each unit in some shape as carpet, paint etc? 

I'd have to run sewer and all utilities to it, as well as do a studs down remodel (it actually has good bones and a reletively newer asphalt shingle roof). 

What are the thoughts on shingling over a layer of existing shingles? 

We have T-Lock shingles in our area and they're so prone to failure that insurance companies have stopped insuring them, forcing roof replacements.

My next project is removing a skylight and replacing with shingle roofing - this has just become a necessity for me because I contact a bunch of companies whenever I have a project, most never respond, those that do are either booked up or never show up to give an estimate, etc etc - requires me doing it myself!