I have replaced several roofs on my multi-family properties in the Syracuse area over the past three years and have generally been paying around $450/square (that includes complete tear-off of the old shingles). 

Lots of deferred maintenance, not major things, but stained asphalt shingles, gutters need replaced, brick building need power washed, a couple of the fascia and soffit boards need replaced, all trim needs painting, ugly amateur ceiling repair where leak occurred, missing drop ceiling tiles in bathroom, no landscaping.

You just need to make sure that there are no cracked shingles and if there are you should be replacing them ASAP with cement siding to match

The upstairs also needs the floors refinished, painting, cleaning.The decks were okayed by an inspector according to the current owner but they look like they don't have many years left.The yard is like a jungle so it needs to be cut/trimmedSome of the siding shingles needs to be repaired or replacedThey ran new electrical wiring upstairs but it needs to be connected to the box in the basement.The owner has agreed to remove the dumpster currently in the front yard and clear out all the "trash" there before it sells.ARV: $98-102,000Repair costs: $20k on the mid/high sideUsing 70% of ARV and an assignment fee of $5k it looks like my MAO would be about $43k.  

What type of shingle to use.I'm all about long term, so I don't mind spending a bit more for more quality and what not.

There are heavy stains on the North facing shingles and the granular material is loose on shingles, which are signs of wear and age and indicate that the roof may be nearing the end of it's useful life.

But, while I was on the phone with him discussing options (shingle vs metal), he lowered his quote verbally by $500. 

Early September, while I was visiting the town where my duplex is located, I noticed a few shingles missing from the roof.

It is fairly easy to get by with the computer abilities now-a-days.  

The owner must grant such access to computerized or other electronic records & to any computers, facilities & must provide any information or assistance needed to access the records.5.