Should I try a nipple shield to relatch ???

Hi all. My son will be four weeks on Thursday :) he is happy and healthy. I started off breast feeding but my recovery after labor was so hard, and even though my boy was latching- breast feeding left my nipples so sore and cracked!!!! I wish someone would have told me that that’s normal in the beginning.... I ended up pumping and it was much nicer on my nipples so I became an EP. It’s not too bad, but it’s really hard to take care of baby while pumping every three hours, especially alone. I have considered trying to get my boy back on the boob. He will latch, but milk won’t come out? Would a nipple shield help with this? Those of you who breast feed, how often do you pump a day?