I played TSO too, I think I was 13 or 14, and the $10 a month thing did suck back then. hah. I liked the game and think I played it for several months but after a while it became kind of stale for me.
I was super happy though when I won the prize for one of the maze houses ^_^ I think it was like 1million simoleans or something. The game was rip with money transfers to different worlds, lol, I did some of those myself. I remember the pizza making job and having to work with other people to make a good pizza. I knew of people that got married in TSO to other simmers, I think I was a shaman at some point too.
I did like the socializing part but to me it became the only concept of the game, just getting online to talk to other people lol. My sim didn't really have a fulfilling sim life like the kind from regular sims. I also think that is in part because it was Sims 1 style and back then sims didn't age and things were home lot based. If they tried to do a f2p sims online concept I might try it out but I'd need to have my sims be able to do more of the single player stuff and not just chat all day =D