Era was dope as hell when there were only like 15 different guns, only grenades and mines and like 3 melee weapons.
Era had(has) a progression system that classic didn't. While you were making money doing jobs or whatever, it was to get a better weapon to become better. Classic was just getting more cosmetics.
Also, there were only like 20 relevant gangs back and 5 bases which made basing more personal because you knew the people in the other gangs.
Most of my fun however was because of the people I met, and the fact I was the leader of one of the most high profile gangs on the server with my own personal friends, not randos.