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.

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!

Update:According to the inspector, the roof needs to be changed out soon because the shingles are cracked, some spots are showing the foundation that it is glued onto.

No tear off , right over the shingles .  

I am assuming they are computerized, and not using typewriters and mimeographs to produce the documents, so...  20 minutes?