Sorry for my inactivity, I have been extremely busy with work and other things lately.
So what was my worst moment in a digimon game/anime? Well I was playing Digimon World 4 and I was grinding for Tech points on my Power Down skill. After grinding for about 2-3+ hours, the game freezes on me and I lost my grinded tech point skills and the two new skills I learned. After that, I started saving frequently but I don't have to worry about that anymore because that was back then when I was still using my semi broken gamecube. (The open button was messed up and would occasionally get stuck and it would be hard to pop it back out and plus the disc reader wouldn't always work correctly) But whenever I would play it on my wii, it would never crash.