I EP'd for just over a year with DD, and am hoping to avoid it this time. But, I would say that while it was a lot of work, I actually think (in retrospect) it was a good experience... and wanted to share some of what I learned.
First off, I didn't have any supply issues. Right off the bat, week one I developed cracks that got worse, and worse, and worse - to the point that I was on APNO cream and my midwife wanted to stitch my nipples! 3 lactation consultants, weekly support groups... And I started pumping at 5 weeks. At first I did hand expression, but that only lasted a day or so until I broke out the pump (often would combine the two for maximum output). I initially pumped every time my DD fed (on demand, not scheduled) and always pumped an extra 5-10 minutes when it seemed my flow had stopped (usually could get at least another ounce). This I kept up for at least 6 months, and then when I had too much frozen (100+ oz) cut back to just scheduled pumping. Cutting out the overnight pumping was a great feeing... especially when I could pump 12-15oz in the morning! But, I always pumped at least as much as my DD consumed in a day - no matter what.
I've heard that low supply with pumping can be an issue of the size of shields used with the pump - and if they are too small they can restrict your flow.
I also looked into foods that would help supply, but never took more than a multivitamin, drank a TON of water, ate many snacks, etc..
As for the 'how to survive and have a life' issue - I pumped everywhere I went. My back up plan was always to pump in the car using a nursing cover for discretion. I used the Medela Pump in Style, which has both a car adapter and battery pack. Basically, I would try to arrive early to places, pump in my car, store it in the little cooler with ice pack, and go about my business. My DD had her bottle of milk ready, and what I pumped could be used in case she needed extra. It was common to also pump before I headed home or immediately when I got home.
The last month or so when DD was eating solids, I started to lose supply, and then would "power pump" where I'd pump every 2 to 3 hours (even overnight) for a weekend (a good 2-3 days). This would increase my supply again, and get me through another 2-3 weeks without issue.
Double pumping was critical for me, because it cuts pumping time in half! Plus, I had a lot of support from my husband which was crucial! I think for me the key to success was overdoing it in the beginning, and then cutting back when my supply was stable and ample.
EP'ing is hard and very few people understand it. I felt BF'ing momma's wondered what I did wrong, and formula momma's wondered why bother, and personally, I was truly devastated that I could not BF. But, in the end, BF'ing was very stressful for us! VERY stressful! EP'ing was the best solution and allowed us to replace painful, tear-filled, tense moments of feeding with calm moments of bonding that I'm grateful my DH could also share in.