Yeah, you're absolutely right. If a player loses their gladiators on day 40, it would be really tough to catch up using fresh recruits.
My only concern is that if someone has a high-level gladiator, they could farm low-level enemies indefinitely to earn easy money. Since earnings are based on Charisma, a high-Charisma gladiator could make over 200 gold per day with zero risk.
Hmm... I could maybe implement a system where, if the combat rating difference is too large, the match can't be scheduled. I’ll need to think this through.
Thanks again for your feedback, really helpful.