There are a few things I want to "address." First, I'm assuming you want to continue to breastfeed your son? Or are you wanting to wean him from the breast and give him breastmilk exclusively from a bottle? From what you've said, I'm going to go with the first option...
Second, I know pacifiers are a HUGE personal issue for some moms, but I found that my son NEEDED a pacifier because of his constant need to suck, which is normal. I thought I would be the type of mom who wouldn't mind having baby attached 24 hours per day, but it really got old and tiring, and I couldn't do anything else during the day. Depending on how you feel, he's at a good age to introduce both a pacifier AND a bottle.
I agree with another mom about you not necessarily needing to increase your milk supply, but you're definitely going to want to start stocking your freezer for when you go back to work. Check out the milk calculator at http://www.kellymom.com/bf/pumping/milkcalc.html if you have questions about how much your little one might take each day. Keep in mind that most bottle-fed babies take more milk regardless of breastmilk vs formula!
As far as pumping goes, you have a few different options, and a few other moms have already commented on them. Whatever option you choose, you can always change it, and be prepared for an increase in your milk supply regardless of which you choose :) You can feed on one breast and pump the other (either at the same time or right after he feeds). Try not to limit the feeding to one breast and the pumping to the other. Change it up because your baby will ALWAYS be more efficient than a pump, and you don't want your milk supply to decrease in the pumped breast! You can feed on both sides, then pump both sides simultaneously right after you feed for about 5 minutes (or about 2 minutes after you get the last drop of milk). You could also start with 2 pump sessions per day (which may be all you need depending on how soon you're going back to work), normally being right before YOU go to bed and right after his first feeding in the morning. When you go back to work, you're going to need to pump whenever he would nurse while you're away to maintain your milk supply. Remember it's all about supply and demand, and what goes out will come back in!
I'm a peer counselor with Nursing Mothers Counsel, and I'd love to help you prepare for the transition! You can email me directly at ____@____.com or you can call our hotline at (650) 327-MILK. We're all nursing moms and offer FREE, non-judgmental information to nursing moms at all stages of breastfeeding. You can also check out our website at http://www.nursingmothers.org; we have many information sheets that you can look through and read. You can also try one of the following books:
The Nursing Mothers Companion, Kathleen Huggins
Breastfeeding Made Simple: 7 Natural Laws for Nursing Mothers, Mohrbacher/Kendall-Tackett
The Ultimate Breastfeeding Book of Answers, Jack Newman, M.D.