I haven't tried out many of the custom worlds yet, but am curious about them. I've seen Roaring Heights featured in some LPs and love the look of it. I also am a big fan of fantasy so Dragon Valley looks interesting to me, but I'm sure I'd need to mod it up a bit to remove cars and computers and things like that to give it a proper "ye olde" feel.
I usually like worlds that have lots of extra space to plop down some extra lots if needed. I've always loved the autumny-look of Appaloosa Plains, but was annoyed that anytime I found a good spot to plop down an additional lot, there were thick fences around all the streets in those areas making it impossible to add them in and use them so you really were limited to just what the world came with by default. Riverview, on the otherhand, was quite easy to add extra lots to, and I still quite enjoy using that world, even if it's considered a "classic."