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Personally, I've never completed a Pokedex completely. I want to say I was in the mid-100s back when I had my gold/silver cartridges, but I kind of find it pointless now that I only play ROMs.
Definitely the hardest has been Regice. I had to restart my game about 10 different times, and I had 20 ultra balls + 10 great balls per restart. Since he has lower PP moves, he would run out and start struggling, ending up killing himself before I could ever catch him. What a punk.
Day 2 (Last night):
Vulcan the Adamant - Level 58 - Male
175 HP / 146 Attack / 103 Defense / 108 SP. Atk / 112 Sp. Def / 154 Speed
- Overheat
- Stomp
- Bounce
- Ember
I kind of screwed this up on accident, but Ponyta/Rapidash's moveset is weak from the beginning, so I might have a hard time...