I certainly appreciate you taking your time to read this and respond :)
What I think you may not be considering, however, is that things changed since you started playing the game. Even for those teams that started around season 20, many teams did not have "complete" arenas yet. Right now, however, almost every team DIII and up in the US has one. There's a certain point when it stops feeling like "raising from nothing against stronger teams" and just feels like you're playing one big game of meaningless catch up. With me personally, I've felt like quitting several times over this specific issue.
Take your arena, for example, LA-Kareem. It costs over $6.6M to get to where your arena is now, which, assuming a weekly income of $130k which goes solely into an arena (I think this number is in fact much lower for most teams), will take a new manager a calendar year to catch up to you. Who would want to play a game that takes a year of their lives just to get to where you are. This isn't a strategic choice - any moron could decide to pour all of their money into their arena.
All in all, this game is so good at not giving too strong of an advantage to people who pay, people who spend a ton of time on the game, and people who try to accumulate a ton of money and then make a run for the championship. To me, managers who have stayed for more than three years have a huge advantage over newer players in terms of arena size. To me, having to spend a year pouring money into an arena majorly discourages many managers from sticking around. Ask yourself, if your arena alone was halved today, would you continue playing this game? Or would find the whole process of building it up so tedious that it wouldn't be worth it?