Hi K., I am struggling with this same issue. I am breastfeeding my second child and she's almost 6 months now. I work full time so I pump 3 times a day at the office. I get a lot of milk when I pump, which is unusual (I use the Medela Pump In Style and I tend to get 4-5 ounces every 3 hours). I breastfed my son for 8 months when my supply dried up because I was 3 months pregnant again. Here's what I have done to make it easier, because I truly do want to breastfeed as long as I can.
I have 3 sets of pump supplies, so I don't have to spend time at work washing them, if I don't have the time. I pump for 15 minutes each time I pump. I pump at my desk and can actually do it hands free. I found a position that works, and I put my shirt over the tops of the pieces to hold them in place.
Supply: Are you double pumping? That helps get more. Also, I eat oatmeal every day for breakfast, which is supposed to be good. I saw someone mentioned fenugreek - I haven't done this but I have heard it works well too. I read advice at kellymoms.com (not sure of exact spelling but you can google it) and found that to be helpful.
For both my kids, when 8-16 weeks old, I pumped immediately after the first feeding of the day, and that was "excess" milk that I have frozen. The more you do this, your supply will increase. I also pump after the bedtime feeding.
When you feed your baby during lunch, bring your pump, and pump on the side that's not being nursed on - this will get a good pumping amount and over time increase your supply.
People in the US have such weird issues about breastfeeding. The way I get around rudeness in the workplace is I talk about having to pump, and I dare someone to say something. I travel for work, and I have left meetings saying "excuse me, I'm a nursing mom and I need to go pump". With women colleagues who are mystified, I offer to let them see how it's done. When they see it, they have a new appreciation for what I'm doing. (Moo?). :)
I have gone on 3 business trips and pumped EVERYwhere under all conditions. Including sitting in my seat on an airplane. I just draped a blanket over me and did my thing. My first business trip was when my youngest was 3.5 months (very sad for me) and I brought all the milk home on the airplane - over 90 ounces in little plastic bags! (replaced all the frozen milk my husband had to use while I was gone)
So here's my advice. If you want to keep breastfeeding (and I totally understand wanting to stop and weighing what's REALLY best for the baby - which first is a happy mom), make pumping easier - disregard what people say, buy a couple of extra sets of parts so you can do the washing at home, pump when you can - even 5 minutes is good, use the batteries instead of dealing with plugging it in, buy those Medela pump wipes so you can just wipe everything off instead of having to wash and dry the parts. Drink lots of water too!
I hope this is helpful. Whatever you do for yourself and the baby is the right decision. I love that I've been able to breastfeed, but I know it's not possible for everyone to have the same experience. Whatever is right for YOU is what's right for the baby.