Thanks for the debate and feedback, allow me to interject a few things for you all to chew on:
* The Hall of Legends is exactly that, a Hall for Legends. As such not every gladiator you buy and train is going to make it. Some will, some will not. The average win ratio for the current gladiators in Primus is almost 55% so many are very close to the magic number, it's not some impossibly difficult goal to achieve. If you don't think your current gladiator(s) have the chops to meet the requirements then ask yourself if you are better off selling them and buying a new slave to start over and try again. Only you can make that decision. Contrary to some beliefs, non-HOL slaves are still very capable of meeting the requirements and with many top gladiators being promoted into Seasons periodically it will become even easier.
* You can't predict future wins and losses in Seasons from the first few days of combat. In the beginning everyone is rated the same so stronger opponents are matched with weaker ones more often until enough battles play out and "correct" ratings are established. At that time if you have a gladiator who was winning or losing a lot that will very likely change since they will be matched up more often with other gladiators of a similar rating.
* Each Master has to decide what they find enjoyable in the game. If always being #1 is the only thing you find enjoyable then by all means you'll want to do what you need to in order to make that happen. If on the other hand you are the "it's the journey not the destination" kind of player then make whatever decisions you need to in order to achieve that goal and find what you enjoy.
* If at a later time it proves too difficult for gladiators to meet the requirements we'll revisit it and make appropriate changes. It might be a modified version of something like Cyn suggested or something completely different. I don't think we are at that point right now though, however, I'll keep my eye on it.
Good luck in the Pit!
-Nate-