Item Hunt tended to be one of the best ways for me to turn a profit up to about level 60 back when I was more concerned with earning SP than beating IH...then after a series of not-that-bad expenses and losing only about 20mil, I beat Item Hunt and obvs now I can't start another round 'cause I'm at 100...

...does it just...stay like that forever? I was really looking forward to getting Chase as a challenger and stuff.

You can't play it anymore because you've beaten the game. There's a thread about it here - Reflection & Item Hunt Changes!.

Thanks for the info - that is a little frustrating that I can't ever unlock Chase as a challenger, though. I s'pose that answers my question :D