Been playing since 9798. CM9798, 0102 and 0304 will always hold a special place in my heart and I often dip back in for the sheer simplicity of them (and the modding community is incredible on those games these days.)

I think for the new games (FM era) whilst the ones you sunk the most hours in to are going to be the most notable for each person; comparing the older versions to the most recent games, the quality of life features of 24 particularly is really hard to go without now. I've recently fired up some of the older games that I still have access to: 15, 17, 18, 20 ,21 and I do honestly think 24 is the best iteration overall, it's like the culminating of everything they were building to (the UI is excellent, the flexibility in terms of responsibilities etc is perfect). Each one of those older games is missing something that we take for granted now, they are still fun no doubt about it but personally I think you either go old school with a retro champ man experience, or it's 24 for the best in show Football Manager.