Pocket had a far better screen than the original GameBoy. Less smearing, more of a proper black pixel color than the spinach screen on the O.G. and better battery life would be the reasons I would go Pocket over original.
When it comes to the original monochrome handheld lineup, the Pocket is probably the best option for most people... or I would say that because it does have two things against it. The Pocket has the better screen (less smearing), and the smaller form factor is a partial win because it fits in my pocket better (hence the name!) but it did come at a cost.
The original "brick" form factor of the DMG units was genuinely good to hold, since it felt solid and felt not too far off from a NES controller. (fun fact: you can exchange the controller parts between an NES and Famicom controller and an original DMG) The Pocket is great, but the slightly smaller size does make it a bit more annoying to hold and do certain inputs with if your hands are pretty big. So I guess it's a tradeoff.
Additionally a small but often overlooked detail is the sound quality. You'll see LSDJ chiptuners bitching about this day in and out and I know most people probably don't care but I think it's worth mentioning. The Pocket has "worse" audio than the original Gameboy simply because it filters the audio too much causing songs to sound like they don't have a lot of bass to them. The Color models are arguably worse about it, though.
Also, since I'm referring to the entire original monochrome GB lineup, then the Pocket gets blown out of the water by the Japan only Gameboy Light. Because it's a Pocket but with that "indiglo" lighting that most watches would have (IIRC, it's called electroluminescence). The only downside there is that second-hand Light models are retarded expensive, with the cheapest ebay listings often starting at $120 with myriads of problems such as broken LCDs. But if you get your hands on one you basically have the best model on hand, as long as you don't care for the sound output. Hell, I'd take it over the Color in many cases simply because I can play it in the dark.
But that said my main complaint with basically any pre-Color model is the fact that the contrast between gray/green shades is fucking horrid. And for this reason is typically why "bivert" mods exist for the things. As much as I liked my time using a GB Light, no biverting meant that the screen didn't contrast as well as it should and applying a giant fuckoff greenish glow to it didn't exactly help.
Oh for sure (though I love me some chonky DMG form factor). For context, we were talking about GBC and Pocket
One reason is probably because without knowing button codes, GB titles on GBC kind of have this really shitty looking palette with red objects and green sprites. Pocket/DMG on the other hand are entirely in the grayscale realm.
edit: I forgot that a lot of the early launch titles actually have weird builtin palettes on the GBC
edit 2: spelling
(I meant to post the above much sooner but never got around to it)
Is the Chromatic worth it? I've read that it looks a lot better than the drop in screens, but it costs so much.
I've not used it but I heard it's really good. I think for most people it's good if you're just casually playing but hardware purists won't give a shit and I've heard about it having dubious compatibility with weird bootleg carts, so if that's your sort of thing I wouldn't suggest it on that front. But the best part about it IMO has to be the screen being really good out of the gate and not a hardware modfest to have a good screen. It also IMO blows the Analogue Pocket out of the water.