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Answering your questions in order:

1. Yup. My purchases are usually motivated by whether or not the brewery is local, how cool the label is, whether I like the other beers I've had from that brewery, and sometimes my Untappd recommended list. I buy almost exclusively singles. I've only been drinking for about a year so I still have lots of beers to discover, plus I just like trying new things.
   
   
2. Stored cold and served chilled is best. This is a decent ballpark for serving temperatures, but in general, the darker the beer goes, the warmer it should be served. I usually just warm up my glass with my hands for 30 seconds or so if it's a darker beer.
   
   
3. Glasses are generally either bought in sets in stores like these or bought singly from breweries people like.
   
   
4. What /u/tinoynk said is true, a flight will usually be a good way to try new stuff. If your local liquor store sells singles, a make-your-own-six-pack is a really good way to try new beers. Try a lot of styles to figure out what you like. If you're really stuck on what to try, the app Untappd (if you don't already have it) allows you to log the beers you've had, and suggests new ones for you to try. Alternately, post in /r/beer asking for recommendations (they're usually very helpful to newbies).