Well, kind of. DS and DD turned 7 the day after DD2 was born. We had a really rough start to bf w/ the twins, but they nursed forever (DS weaned at 6, about the time I got pg again). I expected DD2 to be easy to bf, after all I knew SO much more, was having a homebirth, had a great "tribe" of friends who were bf moms, LLL Leaders, IBCLCs . . .
Knowing more certainly helped (nipples shouldn't be more than tender and certainly not cracking. . . good sign to get some help!), as did having that support network. But it's not all about what you know, baby has a part to play, too. DD2 had a tongue-tie so it took some time and intervention for everything to go smoothly. And nursing an older baby/toddler is so different and fills so much more of your nursing time than those intense newborn days, that even with years of bf experience it all seemed pretty new and hard at first. I remember at one point, with sore nipples & a baby who had to learn how to latch after her TT was clipped, thinking "I HATE breastfeeding" and feeling so guilty that I didn't love to nurse this new baby. It took a lot less time and trauma to work through our issues w/ DD2, though, and I quickly got back to loving nursing.
Ed. - Forgot to add, I think it's so wonderful that you pumped for the baby. I have one friend who was a surrogate and one friend who has twins through a surrogate and they both looked at me like I was nuts when I asked if their babies got breastmilk.