BF advice

When I started feeding at the hospital, my son latched right away very strong. My right was more comfortable from the start. After a day, I got a blister on my left but kept feeding through the discomfort until a few days later when I couldn’t put him on it without yelping in pain. I gave it 2 days off from nursing and used creams, silver & hand pump to keep supply alive until it healed. After that, I was nervous and used a nipple shield on that side. Fast forward two weeks and I’m tired of the shield because it’s so inconvenient and I’m worried it’s effecting my supply (my right boob is so much bigger and I catch so much extra with it). I’ve also noticed my left nursing sessions are always longer sessions than on my right. so I’ve started nursing without the shield. Question 1. Will losing the shield help me up my supply with my left? 2. It’s still a little sore while nursing on left, how can I fix this? His latch looks the same as the other side but it is a shorter nipple. 3. Should I be offering both breasts even when baby falls asleep after a long nursing session?