Well, if you go into it with a certain mindset, you should be okay.
The Mindset: this is an older game, so you're not going to be able to win at all the events and challenges they provide. As with anything, the more characters you have, the better you will do at all these things.
As you build your characters, you'll be able to progress more and more.
If you were to start now, I'd advise you to concentrate on progressing in the main story line and level those characters to 10...understand how the game works and the season aspect.