Yes, definitely give resorting a go! As many have mentioned already, it is a fantastic opportunity to challenge your imagination, meet members that you might not have played with in your original house, and, well, it is a lot of fun -- which is what RPing is supposed to be all about!
My first SS sorting landed me in Hufflepuff, which is the house I identified myself with before even joining the site. I played a number of characters in Hufflepuff as resorting wasn't an option back in the day. I played Zoe Koboi and Amanda Madigan, which were my very first RP characters. I never really was satisfied with them because I was a newbie and had no idea what I was doing, which is why I didn't keep the same character term after term in my early RPing days. But getting involved in the RP inspired me to create new characters that were more complex and meaningful to me. That was when I fell in love with my characters Tancred Adara, Seth Paton, and Demarcus Diggle. While all of these characters were in Hufflepuff, it was fun RPing them because they were very different from each other.
I did resort to Ravenclaw after Demarcus graduated, though. I had the option to do so and I wanted to see what playing in a different house would be like. I will be quite frank: I did not like being in Ravenclaw. Not because of the members and their characters, but because of the "It is so weird for ME to be in Ravenclaw; I want to go back to Hufflepuff" mindset that I had. This mindset held me back from truly exploring Ravenclaw through my characters Marshall Davies and Natalie Pillsbury. I literally forced myself to play them just so I could resort again. This made RPing not so fun for me because I was doing it only to be eligible for resorting. If I had a time-turner, I would give Ravenclaw another shot.
Now I am in Gryffindor, and the experience is quite different than when I was a Ravenclaw. Having learned my lesson, I focused on my character Demelza Diggle being a Gryffindor -- not me being a Gryffindor (let's be honest: I'm a Hufflepuff through and through). I am enjoying being a member of Gryffindor house because I am playing a Gryffindor through my character's point of view, not my own. So, the experience in another house is only going to be fun if you go in with the right mindset.
With all this said, resorting is a huge commitment. If you resort, you are in that house for at least seven terms. There is no going back any time soon. It may seem scary, that you are "betraying" your house, etc. However, keep in mind that many resort to challenge their imaginations, meet new people, and have fun. Resorting to a different house is what you make of it. If you go in with the mindset of "This house isn't for ME," then you won't have much fun. But, if you resort for the right reasons, then those seven terms will fly by with ease.
If you are still having doubts or second thoughts about resorting, then maybe it isn't the right time for you to so. There is absolutely nothing wrong with that. We all are attached to our original houses in some way. But if you are even the tiniest bit curious about playing in a different house and/or are still sitting on the fence when it comes to resorting, then I suggest utilizing the
Knockturn Alley (Role-Play) forum, playing different characters in Diagon Alley, or trying out characters with your friends outside of the SS RPGs. Once you have dipped your toes into the "unknown" and found that you enjoyed and are comfortable with it, then fill out the resorting form and begin your new adventure!