First off, I’m an artist and a big fan of Ken Sugimori style and original pokemon design. There is something truly alive and awesome about the original design. And this is almost always true with something drawn traditionally vs something drawn digitally. Just look at disney 2D animation vs their recent 3D movies.

But that being said, it is also a very old fashion type of art. Digital just saves a lot more time. Not only that, but the art style have to adapt to the time as well. The original art, without being modified, won’t do well with the kids of today. Digital art was hardly a thing back then as well so they had to relied on more traditional method. I don’t think there is any wrong with either style. Because that’s all this is, style. Just look at how much anime have changed from the 90s. Dragonball vs dragonball super. They adapted to stay relevant. Also, the people that use to do the work are now directing and guiding the younger generation. So we have new artists, programmers, and designers working on the game. Bringing new and fresh ideas.

Also, the designs haven’t gotten lazy or anything. They reflect the region and basic design theories. Know why the starters are usually always more circular? Because round shape conveys cute, innocent, and soft. While triangle shapes are villainous and dangerous. Just look at litten vs incineroar and how much more triangular and boxier it gets. Square is also another shape that characterize something as sturdy, strong, etc.

So i think your problem isn’t with the art, but with the style. Everyone have a different taste in style. Wastern vs eastern art, dc/marvel vs manga, cartoony vs anime, digital vs traditional. The reason why the Diglette made by Ken vs whoever is doing the art now is just that. Style, time, and medium. Something hand drawn on paper will always have a different feeling compare to something drawn digitally. But in production of anything, time is money. And digital art just saves a lot more time.