I suggest trying laid back positioning. You can still hold baby in a cradle hold, you can hold baby in any position in laid back, some moms find it works best to latch baby first and then relax back. Also you can be reclined as much or as little as you like (but not flat on your back.)
I've tried a few positions and have found the cradle works best for us (with the help of the lactation consultant). The left side is a little more painful than the right, but usually just in the first couple of seconds. She also tends to buck back and pull, which I think might indicate the need to burp (she pulls off after yanking and when I pat her back, she burps... sometimes spits up.) I've tried lanolin cream which helps, but my nipples don't look cracked or bruised. A week ago, I did have a blister, but that has healed up. As far as engorgement goes, she's recently started sleeping 6-8 hours and I wake up at the 6 hr ark feeling very full. Twice, I've pumped to relieve the pressure and stored it in the freezer in case I might need it at a later time. Thanks for your concern!