I hear there is a major update and new season coming next week. Is it bad to log in now (like I'll start a timer) or should I wait until the update?

The current season ENDS on February 15.  The season after that will probably start a week or two later.

The timer you may be referring to is probably the Olvia server 30-day timer.  That does not affect seasons at all.

So if you have current characters and stuff you'd like to work on like journals and such, you can log in now and wait to create new characters once new season starts.

Or you can go heavy on the current season and do everything in the week that's left.  It depends on what kind of player you are.

Cool thx!