It's been said you can tell who the winner of a competition will be by observing who is the happiest to be there.
To draw a parallel with your question, I remind you that to preform well you can't be too result oriented. Ideally you want the results, but at the same time you want it to simply be a joy to play, and you can play for the sake of playing.
Why will you make an effort to travel and compete against stronger players? Why do you play tournaments at all? Remind yourself of your core motivation for playing chess. Losing every game wouldn't be fun for anyone, but if it happened to you (again) will you be sorry you went?
What if you played fearlessly and pushed a strong opponent all the way to the end only to lose in time trouble for example? What if you played timidly, and after mutual blunders you won or drew on move 20? How would you look back on those games a year later? Results are probably not your only personal measure of performance.
All this to say, I think either section is fine, but either way do some introspection and clearly decide what your motivation and goals are. If you can do that I think the choice will be much easier, and in the end it may not even seem so important.
I've been battling with this question all week and I want some advice on it.
I'm registered to play in the National Chess Congress next weekend in Philadelphia, and I'm currently signed up for the U2200. My rating is 1841.
I have a terrible record against experts in my chess career, and I was hoping to play a good deal of them in this tournament to try to gain experience and maybe win a game or two. But...
I worry it will be too much. As it stands I'm right at the bottom of my section and I think I may lose all my games.
If I switch to U2000, I will be slightly below the middle of the pack, and I'm confident I will do well, but I'm not sure if U2200 will be a better opportunity for me to play stronger players. I'll also be under more pressure to get good results in the U2000 section, and the last time I went to Philadelphia to play chess, I played in the Philadelphia Open U2000 and had by far the most embarrassing tournament performance of my life, losing five games in a row. I think I'm better than I was then, as I've done a lot of training and studied quite a bit, but that just goes to show that U2000 could be difficult also.
The other option is to do U2000 now and play U2200 at the Eastern Open in December or something, which may be a little easier since the sections for that tournament go Open-U22-U19 instead of U20.
I am very conflicted so any advice would be appreciated.