That's cool.
I won't really use myself as an example since I always planned to be a stay-at-home mom, but I was definitely the independent working woman and once the baby arrived I couldn't imagine working outside the home (I did continue with home based consulting and freelance work for a while to help with the transition, though). I started on forums virtually at the same time as sozlet was born, and sometimes it still brings me up short when someone says something about me being maternal, or something -- WHAT? I'm boss lady, high-flying professional woman, ME. Up until 6 years ago, that stay-at-home mom stuff was just totally at odds with who I was.
At any rate, while that's my experience, my comments are are much more based on what I've observed -- other people IRL or whose stories I've read on forums.
On to other stuff:
I know that breastfeeding does hurt for some people so I won't make any blanket statements. But for me it was by far the easiest part of having a baby. Baby's upset? Whip out the boob. We're both tired and cranky? Whip out the boob. Baby's bored? Whip out the boob. Baby's sick? Whip out the boob. It solved so many problems so efficiently, and was such a nice respite. And that's not even going into all of the indirect benefits -- baby being sick far less than she would otherwise, etc. I'm sure you know the stuff about the process releasing euphoria hormones (hormones? something), so even if you're cranky when you start you are feeling so much better and more able to deal with things by the time you finish. And that's not going into the bonding, how the baby that was driving you insane five minutes ago suddenly becomes the sweetest, most beautiful creature on the face of the earth. For me, I can't imagine how much harder that first year or so would've been without breastfeeding.
So I really think that the benefits of breastfeeding as much as you are comfortable with outweigh... pretty much everything. If you're uncomfortable -- because I know that does happen -- that's a different story.
You should be able to take breastfeeding down to 2-3 times a day, yes. Easier if you pump for the intermediate ones (pump breastmilk, store, caretaker serves to baby the next day while you pump, etc.) but I think that you can just keep reducing to whatever works. That's what happened when we did wean, anyway. Went from very often to less often to less often yet -- by the end it was just a nip here and there. I remember she went for a week without and then when she tried again, there was still some milk (if not much). La Leche League is a good resource there.
www.lalecheleague.org
I know this stuff is scary, though. The more you learn, the more managable it seems (at least that's how it worked for me).