I have entered a couple times in our local fair and being judged wasn't the difficult part for me, I have no problem hearing an opinion from the quilt police it's still fun to see your work displayed. The hard part for me was leaving my quilt at the fair for so long, I was so worried what if it was stolen, what if there was a fire, or vandalism? I'm always happy to get my quilts back safely. I know it sounds silly, but seriously that was my concern.
I think you should enter.