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Best way to level up in the older games?

Victory!

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In my attempts to play every generation, I've found that leveling up and keeping up with the opposing trainers (and sometimes just the wild pokemon) to be a very slow and tedious process. Now, it's not like I have a lot of Pokemon, I've nearly always scaled the size of my team to my progress. Generally asking advice for everything from Gen 1-7
 
  • Use items like the Exp Share and the Lucky Egg.
  • Have the desired Pokemon in front of the party and change it out first turn.
  • Train 2-3 Pokemon at the same time, specially in Gens 6 & 7. They'll not get as much EXP as the one in the point above but with time they'll catch up faster than you'd think.
  • Battle evolved Pokemon, they give out more EXP than usual. Also, be in the lookout for Pokemon that give out more EXP than the others like Chansey, Audino, Gyarados, etc.
  • Don't be afraid to battle the league multiple times, it could be hard the second time but it'll get easier every time.
 
You have to level grind, which may involve several hours of tedious battles, but that's how the games operated back in the day. I'd also suggest Lucky Eggs and using traded Pokemon which level up faster, though in some of the old games Lucky Eggs are incredibly hard to obtain, and trading may not be practical or even possible depending on how you're playing the old games.
 
Specifics are going to vary by game. In any entry with the Vs. Seeker I don't think it's generally too bad. Good rules of thumb are not to try raising more than a full team, explore every area thoroughly without skipping battles, and to resist the urge to use Repel in new areas.

Also, it's okay if your levels are lower than the opponent as long as you're still winning--in fact I'm pretty sure until Sword/Shield hte games were designed around the idea that you'll be lower level than major opponents. The player's Pokémon are stronger than their level indicates after a while (especially in gens 1 and 2) and you usually have a larger team than your opponents, especially in later games.
 
In HGSS, I recommend using the area above the waterfall in route 47 and the grass on route 44 that requires surfing. Some of the stuff you get there give apmewhat better EXP than in other areas at the time and they aren’t filled with mons that explode on you. I think it works well for the time in the game once you have access to them.
 
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