It sounds as if your previous pumping experience wasn't a great one. As such, and being a breastfeeding counselor (with Nursing Mothers Counsel in the Bay Area), I'm not going to try to talk you into continuing breastfeeding. When to wean is a very personal decision.
However, each experience is different, and it sounds like you didn't have the proper size of flange during your last expressing experience. If you don't mind a recommendation, try finding a lactation consultant who has experience fitting pump flanges. Part of successful expressing is pump fit, and that includes the type of pump. I helped a mom a couple years ago who found it easier to hand express, and I have a great video if you're interested in that: http://newborns.stanford.edu/Breastfeeding/HandExpression...
If you're intent on weaning, go slow. We recommend 1 dropped feeding every 3-5 days to allow your body and baby to adjust. Have someone else give the supplement (expressed milk, formula, etc), so baby doesn't get confused and refuse the alternative feeding source (bottle, medicine dropper, cup, etc). Not everyone uses a bottle, but it is generally easiest on the caregiver.
We never recommend a particular brand or nipple, but try to use a straight bottle that will hold about the same amount of milk that your baby will drink. i.e.: use a 4oz bottle if baby will eat 2-3oz at a time. This decreases air in the bottle and decreases the chance that baby will ingest too much air, causing gas. The nipple should be soft, not rigid, and should have a longer teat on it.
kellymom.com also has great information: http://www.kellymom.com/bf/pumping/alternative-feeding.html
And here's just a great article I came across a couple of years ago that I share with any breastfeeding mama :) Every month matters, so great job, mama! http://www.drmomma.org/2009/12/if-you-nurse-your-baby.html