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It depends if the team is for competitive battling or just for the storyline. I have loads of 100's in boxes for Wifi,though for my storyline team it's in it's 80-90's.Then I put them in my PC later on,never gotten back to them since I see no big use for them.
It was difficult to train them but I did get use to the time consuming and it gotten easier.
I got my whole team in Crystal to level 100 due to the fact that I didn't have to worry about EVs. They were my story run pokemon though, so I used them for every single match, failures included.
No I only have Charizard and Mewtwo from LG at level 100 and my Espeon and Umbreon from Colosseum. They all got to level 100 using Exp Shares and Colosseum tournaments like Mt. Battle I believe. XD
That was years ago, I don't possess such patience nowadays to IV breed and EV train for the ultimate team. =/
Heavens no, I don't have time for all that. I don't take this whole leveling up business seriously, I just want to explore the regions and enjoy the adventure. The highest my Pokes have been is probably 70.