2nd Gen Red leader or Gold leader?

[virus95x]

Brock is quite hard if you don't choose the right pokemon

 

[blue]

Falkner was pretty easy in comparison to Brock. You had a better choice of Pokemon that stood an advantage against Falkner's Pokemon, with Brock it was more of a challenge to level your Pokemon up to a certain level in order to learn specific moves to take down his bulky Geodode & Onix.

Bugsy is one of the easiest leaders in Johto, maybe a little struggle with Scyther but all in all I don't really struggle with him. Whitney on the other hand is a right pain, with that Miltank can wreak havoc if you don't have the right moves or method.

 

[Ephemeral Euphoria]

The gen 2 leaders were harder imo due to Whitney and Clair mostly especially since finding surefire counters for their ace Pokes was easier said than done at the time. Sabrina was pretty difficult as well but she's not that tough if you got something like Snorlax along for the ride since you could get that beast before heading to her gym if you played your cards right.

 

[Seth Rollins]

In my opinion, Gen 1 gym leaders were harder. To tell the truth, Gen 2 leaders were easy to beat. (Except for Whitney's Miltank.)

 

[Miss Anne Thrope]

In the beginning, I'd say Gen 1 was definitely more difficult for me.
Brock- pretty simple if I got Bulbasaur, but I generally got Squirtle. And Brock was absolute hell if you got Charmander. (Bulbasaur would have Vine Whip and Leech Seed. Squirtle would have nothing but a measly Bubble, which made it much easier to beat Brock with Bulbasaur even if they both have an advantage.)
Misty- She was particularly hard in FireRed. Her Starmie knew Water Pulse, which constantly confused my Pikachu. I don't even remember if she was hard in the originals or not.
Lt. Surge- His Raichu was sure a challenge for my little Pika and Wartortle! His Raichu was just very fast, and I remember having to save before I battled him so I could restart when I lost to re-challenge him.
Falkner- I usually got Cyndaquil, and Falkner was a breeze. I recall having a Chikortia and having difficulty beating Falkner because of Mud-slap.
Bugsy- Again, with Cyndaquil, Bugsy was a piece of cake.
Whitney- I know a lot of people had trouble with Miltank. I got a female starter and had a female Flaaffy with me. Miltanks lady-charms were no match. In SS, Milk Drink caused a small problem, but I believe I still beat her first try.

So yeah, at the beginning, Kanto was harder for me. But later on as I developed a strong team, both were fairly medium-difficulty. I don't remember having to rebattle any, I think maybe I did with Claire? I don't know.

I'm surprised not many people had trouble with Lenora from BW, I had ditched my starter and she gave me a hard time.

 

[Gyardosamped]

I found the generation II gym leaders to be quite easy compared to their generation I counterparts. The only difficulties I faced fighting the Johto leaders were with Whitney's Milktank, and for some reason, Morty's evil Gengar. @_@ Other than that, the other gym leaders were a breeze to defeat.

As for Gen I, I found Brock to be the easiest (I guess since he is the first gym leader), and Lt. Surge to be of the more difficult. His Raichu gave me a few problems while I was trying to defeat it.

 

[Bounsweet]

Brock is harder than Falkner. Rock-types resist a lot more moves that you start off with (typically Normal-type moves like Tackle, Scratch) and Falkner's birds are way underleveled imo.

Bugsy is harder than Misty. They're pretty close, but Bugsy's freaking Scyther...

Whitney is harder than Lt. Surge. Miltank, I shouldn't have to say much else.

Morty is harder than Erika. Erika was pretty easy no matter which starter I choose, just because of how weak Grass-types in general are. Meanwhile Morty and his Gengar with Hypnosis was a nightmare (no pun intended).

Sabrina is harder than Chuck. Chuck is pretty scary with his DynamicPunch Poliwrath, but Poliwrath's dual typing makes it easier to counter as opposed to Sabrina who uses really great Psychic-types.

Koga and Jasmine are comparable. Jasmine's Steelix might be marginally stronger but the only back up she really has are two Magnemites which are super easy to take down. Koga is overall more balanced so I'd say they're about even.

Blaine and Pryce are comparable. I've never had trouble with either of them no matter which starter I use or team I have. There are a LOT of Water-types to counter Blaine and Pryce's team is a little lacking for the seventh gym leader.

Clair is harder than Giovanni. Her Kingdra is incredibly strong and supported with some pretty powerful Dragonair, and stands out more than Giovanni's team, which was sort of just a collab of semi-great Pokemon.

Kanto - 2
Johto - 4
Tie - 2

Overall, Johto has better gym leaders.​