Are there any recommended manuals that systematically go through a home and explain each fixture that might need maintenance?

and the condition of the house:  visit with them,  ask to use the restroom etc - ask for a cup of coffee to see the kitchen etc- use your eyes first, them if you need talk to a GC with a discussion of what you have seen- do your due diligence before you EVEN think of a Quit Claim deed.  

I have found that wear and tear on carpet, fixtures etc. are minimal compared to having 3-4 or more people in a unit.

Your ALL in cost is only a cup of coffee.I am currently flipping homes in Orange County and teach others how to do so as well.

I am happy to go over the numbers with you over a cup of coffee.

The house is split level, 4 levels, 3 bed, 2 3/4 bath, large two car garage with about 3000 total square feet including the unfinished basement.The house is very dated, harvest gold bathroom fixtures, green stain, 2 hinge flat green/brown stained flat panel (luan) doors.

FYI I am doing a complete rehab of the kitchen and bathrooms and fixtures to make the units have a more modern style.

If you buy all solid gold fixtures encrusted with diamonds, the labor cost will likely be a very small % of the total rehab. 

My token of contribution here is to say that for Dorchester, depending on where you go you will find better deals on C, D neighborhoods; however as far as Medford, we have already missed the boat and numbers don't make sense out there anymore unless you get deals off MLS.Good luck and feel free to reach out - I am always open to get together for a cup of coffee the next time you are in Somerville.Flavio

My question is, should I find a deal first before approaching him or should I ask him out for a cup of coffee and discuss my plan and see if he's on board?