Well the Saucer has plenty of taps if you like chain bars. As for hole in the walls, there are a million but they don't have much selection. B&J's is a decent brewpub. Good beers (made by Saint Arnolds....www.saintarnold.com) But the food is really hit and miss.
Co2 does not go "bad" so you should be fine. When it is empty, a lot of welding supplies will not even look at the hydro stamp when you exchange it. If you need to though...most fire supply shops will do the recert on the tank for under 15 bucks.
100% worth it if you plan on using them with any regularity. It is a PITA to spray out rear sealing faucets just to still have them stick a few days later. They will work, but you will be happier with forward sealing.
I am going to lean the kegging way for now. The difference between a partial mash and an AG beer will be negligible. Controlling your fermentation temperatures is way more important. What kind of set up are you looking at? If you can get one that is large enough to hold a keg and a carboy then...