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Description
Disclaimer! I love gen 2. It was my first pokemon game ever. However, compared to other regions, it feels a bit underwhelming. This is not a "how I can fix it" but a "how I would have done it" and it's primarily based on my ideas and opinions. With that out of the way, let's get started~

Someone asked me how I would renew the gen 2 starters, this is my answer:
1) Making each of them more interesting. With the exception of the water-types, the designs are pretty bland and lack lore behind them.
2) Adding a clearer theme. From gen 6 onwards all starters share a clear theme that usually is involved one way or another in the story or culture of the region.
3) Adding double types. Not a single starter has a double type. Double types are not mandatory, but combined with the lackluster designs it adds to the blandness of the pokemon.

The theme I decided was "traditional festival". Johto is a region much rooted in history and tradition, so I thought that famous Japanese festivals were the perfect theme for the starters. The festivals I chose were respectively the Hanami (flower viewing) for Chikorita, the Hanabi taikai (firework viewing) for Cyndaquil, and the Sapporo Snow Festival (snow sculputers) for Totodile. Additionally, because of the new typings and the new theme, all names had to change. Consider their stats to be on par with the newest starters (with a stat total of the third stage at 530). In the end, the renewed gen 2 starters are as follows:

Hanssom (花 'hana' flower+blossom) [Chikorita]
Grass -->
Cherrtress (cherry+tree+bless, also chartreuse) [Bayleef]
Grass/Fairy -->
Bloomossus (bloom+colossus) [Meganium]
Grass/Fairy

The grass line would be able to learn many Ground moves and a little Rock moves.

Shreuze (shrew+fuse with less common fuze) [Cyndaquil]
Fire -->
Firacker (quil+cracker) [Quilava]
Fire -->
Pyrattechnix (pyrotechnics+rat) [Typhlosion]
Fire

The fire line would be able to learn more Dark and Flying moves.

Tyskin (tyke+skin, also kidskin, also ice) [Totodile]
Water/Ice -->
Crocognon (crocodile+Cro Magnon) [Croconaw]
Water/Ice -->
Glacigathal (glacier+alligator+Neanderthal) [Feraligatr]
Water/Ice

The water line would be able to learn more Fighting and Steel moves.

Description
Disclaimer! I love gen 2. It was my first pokemon game ever. However, compared to other regions, it feels a bit underwhelming. This is not a "how I can fix it" but a "how I would have done it" and it's primarily based on my ideas and opinions. With that out of the way, let's get started~

Someone asked me how I would renew the gen 2 starters, this is my answer:
1) Making each of them more interesting. With the exception of the water-types, the designs are pretty bland and lack lore behind them.
2) Adding a clearer theme. From gen 6 onwards all starters share a clear theme that usually is involved one way or another in the story or culture of the region.
3) Adding double types. Not a single starter has a double type. Double types are not mandatory, but combined with the lackluster designs it adds to the blandness of the pokemon.

The theme I decided was "traditional festival". Johto is a region much rooted in history and tradition, so I thought that famous Japanese festivals were the perfect theme for the starters. The festivals I chose were respectively the Hanami (flower viewing) for Chikorita, the Hanabi taikai (firework viewing) for Cyndaquil, and the Sapporo Snow Festival (snow sculputers) for Totodile. Additionally, because of the new typings and the new theme, all names had to change. Consider their stats to be on par with the newest starters (with a stat total of the third stage at 530). In the end, the renewed gen 2 starters are as follows:

Hanssom (花 'hana' flower+blossom) [Chikorita]
Grass -->
Cherrtress (cherry+tree+bless, also chartreuse) [Bayleef]
Grass/Fairy -->
Bloomossus (bloom+colossus) [Meganium]
Grass/Fairy

The grass line would be able to learn many Ground moves and a little Rock moves.

Shreuze (shrew+fuse with less common fuze) [Cyndaquil]
Fire -->
Firacker (quil+cracker) [Quilava]
Fire -->
Pyrattechnix (pyrotechnics+rat) [Typhlosion]
Fire

The fire line would be able to learn more Dark and Flying moves.

Tyskin (tyke+skin, also kidskin, also ice) [Totodile]
Water/Ice -->
Crocognon (crocodile+Cro Magnon) [Croconaw]
Water/Ice -->
Glacigathal (glacier+alligator+Neanderthal) [Feraligatr]
Water/Ice

The water line would be able to learn more Fighting and Steel moves.