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2. same as 1
3. depends on the game some are not using Steam to know what account you are in, so will mess saves on saves
4. Why not use Family Sharing and not buy a second copy then?
http://steamcommunity.com/sharedfiles/filedetails/?id=183087266
The rest you should be fine with.
Depends on the game. If it is an MMO, some people like to "multi-box" where they use more then on character at a time. This allows for soloing of more content and 2x the abilities.
Overall though, Family Share is the best option otherwise, though if he wants to play one game per an account, he would be restricted since only one account can use the library at the same time. Owning two copies would fix that.
I was also going for more of a generalized reason as to "why" though, not a specific one.
Yes for the achievements and in-line stats. TF2 and DOTA 2 are free to play, so you can add those to both accounts.
Not sure how items work with family sharing on a paid game like CS:GO. May want to ask in that game's forum.
L4D2 doesn't have in-game items, so you don't have anything to worry about there.