I'll be escaping community college soon. A good way to save money, but it isn't terribly thought provoking. Some general questions I have:
1. What are things I should probably take with me when I am forced into a dorm? What shouldn't I take?
Usually the college website has a good list of what they have in each dorm, and it's good to check that first -- or, if possible, to tour the dorms before moving in. I wasn't able to see my dorm before moving in last year, and I ended up not needing the desk lamp I brought because my desk had a lamp built in. (That's not a common example, but you see what I mean.)
I agree about a coffee maker and a hot pot -- although if you have a hot pot/electric kettle, you could probably try pour-over coffee, and it might cost less? And I doubt that you really need a printer, unless you plan on printing a whole lot of stuff when in college -- otherwise it's a whole lot cheaper to print at the campus library or at a Kinko's. Not sure about other universities, but my campus library is open at all hours of the day/night so I can print things then too -- meaning, it's convenient, as well as cheap.
I would also add, re: shopping lists:
- A mini-fridge
- A microwave
- Some mugs, bowls, plates and silverware
- Maybe an extra comfy chair, if there's room in the dorm
- Whatever else you'll need to trick yourself into feeling at home and self-sufficient when you're really not.
2. Are there any colleges that don't force you to do a bunch of bullshit pointless work, or is that a requirement for it to be a college?

That's practically too subjective a question to even try and answer. It really depends on the major, and even more than that, depends on what you consider to be "pointless".
However, I'll say right off the bat that the work is going to be more interesting than whatever you were doing at a community college -- and some of that interest will come from having classmates who really care about what they're doing.
3. Does it *really* matter where I go to college? Is there a point in me working to get into a school with a bunch of rich entitled kids who work way too hard?
It really does matter. Not necessarily for job prospects, but for what you end up getting out of your experience. I actually do go to a school where my classmates are rich and entitled kids who work way too hard -- and I transferred there from a state school. Here's why:
1) I wanted to be surrounded by students who were motivated, hardworking, conscientious, and really cared about what they were doing. At the state school I went to, even though the kids there weren't rich, they felt pretty entitled, because a lot of them seemed to be wasting an education; they didn't care about being there, they were just coasting through, and the classes were so low-maintenance that what you learned in class wasn't even the most prominent part of your time at the school.
2) The professors may have been decent, but the professors where I go now are waaaaaay better, and a lot of that comes from the fact that they do NOT play down to the lowest common denominator. Classes are never easy here; at the state school, I'd take 18-20 credits every semester and have a whole lot of free time, and here I'm working my ass off with 15-16 credits.
There are more reasons, but I forgot them at the moment...
4. Major in engineering? Chemistry? Theoretical physics? What degrees are worth it?
They can all be worth it, depending on your work experience, volunteer experience, and graduate school -- and depending on your career plans. Very few college degrees are not "worth it".
5. What happens if I decide I want to be a doctor?
You take the required classes -- or you play catch-up in your first year of med school. No big deal.
6. Should I do a second year of comm college, or if I can get into, say, Boston University, should I go there? Should I not even bother with an up there public college? How am I supposed to pick a college I will be happy with?
Go somewhere where you'll meet people who will help you grow as a person, become more smart, and think differently. Regarding the quote that I bolded way earlier: that's what college is supposed to be about. If it isn't thought-provoking, then it's being done wrong. So I without a doubt would say BU, over community college.
Do credits normally transfer easily? What are the sort of credits that don't transfer easily?
Really, really depends on the school, and the program. I'd ask the registrar.
Is it good to live in a dorm? A lot of people I know hate it. What is to hate? What is to love?
Love:
- Convenience (it's close to everything!)
Hate:
- Rooming with someone you don't know (not something that bothers me, but it's the main reason why people hate dorm rooms)