Something I'm doing differently that is actually kind of cool, more of a cosmetic thing really, but instead of letting them go when they faint, I made a PC box called 'Grave'. Anyone that faints goes in there and can never be used again. I can go back and look at it and I actually remember leveling each one, and remember how each one died. I think it adds to the emotional aspect of the challenge. Think you're ready to take on the gym? Take a quick look at your grave and remember what happened to your last team when you rushed in too early.. makes you stop and think..
I love these fan made challenges for games. This reminds me of something like doing a 3 heart challenge in a Zelda game. Although I found myself lvl grinding as much as I could and as often as I could. For some reason, you get more attached to the Pokemon you have in your party and when one finally bites the dust it sucks to have to release it.