#2
110 bucks is a pretty good price for a squire and amp. You're not getting anything spectacular. Ask how much it's been played, what type of condition it's been kept in for the last year and half since it was last played, the condition it was kept in while it was played, stuff like that
My gear:

Memphis les paul (fixin it up as we speak!)
Schecter C1 plus
Ibanez RX 240 (been sold)
Peavey envoy 110 (Pretty dang good!)
Some washburn acoustic...
#3
Can't go wrong with a squier as a first guitar. It is a decent deal, just give him 100 for it. Shouldnt be anything wrong with the stuff, but just ask if he has had any problems and if you can see it before you buy. 100 bucks for the whole package would be awesome!
GEAR:
SCHECTER LOOMIS FR
LTD EC-1000
LTD DV-200
#4
First of all, don't let him make you think it's a Fender , and charge you more when you show up, it's a Squier, an offset of Fender that will be much lower quality, so haggle him down (especially on that one, it's a Bullet). The guitar itself brand new is about 99$, I'd say go for it, it's a good deal if everything works. Good luck!