There are times, especially as I get older, that I meet up with a friend from college or a former co-worker who I haven't seen or talked to in years--and invariably, before long it feels like no time passed at all since we last met, and the intervening years were no more than an illusion. For me, re-watching Love Hina feels a little like that. Love Hina was the first digisub I ever saw, back in 2000 when I associated fansubs with big, yellow padded envelopes with VHS tapes inside. I remember being floored by the fact I could just to go to iDrive and download (in 20 or so rar-compressed pieces) an entire episode of Love Hina, in all its 40MB file size, 15 frame-per-second, yellow blocky subtitle glory, a mere week after it had aired five thousand miles away. I had just received DSL through work, and it felt like the megami-tachi of anime had, in their infinite wisdom, blessed me with broadband at just the right moment in anime history, so I could watch Love Hina without swearing at a 28.8k modem and tying up my phone line for hours at a time.
So part of the reason I like Love Hina is probably nostalgia, but even without that factored in, it's still fun to watch. Love Hina's not the greatest anime ever, but what makes it worth watching (and re-watching) for me is its characters--while everyone has their favorites and least favorites, during the 24 episodes you spend with them it's hard not to get at least a little attached to the residents of Hinata-sou. Akamatsu knows bishoujo, and he can be decent at drama too, when he puts his mind to it. It's not a harem series like Shuffle where the girls all fall all over the main character, trying to make him bentou, get him to marry them, etc.--yes, there are a lot more girls than guys in the cast, but the main focus is Naru and Keitarou's relationship. The other girls like Keitarou to some extent, but they also know who he likes and in their own way they work to bring him and Naru together. Akamatsu-sensei is good at creating memorable characters, and with 24 episodes to work with, even the ones that seem one-dimensional at first (Koalla Su comes to mind) get their own backstories and motivations fleshed out.
The most common complaint leveled at Love Hina is 'not as good as the manga', but I actually liked the anime storyline better. Naru's over-the-top violent in the manga, and while the Naru punch gets applied liberally in the anime as well, it seems like the anime Naru has a little more heart to her. Plus she's voiced by Horie Yui, so it's hard not to be a fan ^_^ . The manga also got stretched out into the whole Kanako arc, which just seemed like an attempt to draw the series out longer than it needed to be (and in an interview Akamatsu admitted as much, that his publisher wanted the series to keep going so he added Kanako in to pad it by a couple more volumes). The anime (except for Love Hina Again, which I'm not counting since I'm talking about the TV series) cuts Kanako out completely, and the story seems to flow better as a result.
Love Hina has plenty of "love comedy" staples--there are lots of misunderstandings, punches, accidental groping, walking in on the opposite sex in the onsen, and so on. But to offset all of those moments, which don't really add anything to the plot, there are some really memorable ones, like Sara lecturing Keitarou on the difference between 'dreams' and 'chasing rainbows' (in English, even). Yes, the recurring gags like the Naru punch get repetitive, and I'll be honest, there are a few episodes I just skip over completely re-watching this (the 'detective' one in particular felt like a "we need to save budget this week" episode). Still, Love Hina has a great cast of characters, and I give Akamatsu-sensei credit for doing a good job with character development. Motoko, in spite of being a side character, maybe changed the most during the course of the series, but the way each character's issues are presented and ultimately overcome was done very well--much better than I'd expect to find in a "shonen love comedy" series.
Overall, I'm sure nostalgia is a factor here, but if I had to pick 10 anime series to be stranded on a deserted island with (an island like Kanna's in Happy Lesson, with electrical outlets in palm trees and a DVD player) Love Hina would make the cut. Go, go, Naru-chan!