I will go through each console I own and talk about the D-Pad. At the end, I will give the answer that everyone wants: Which one is the best? Please keep in mind this is only based on the controllers that I actually own, so in several cases the rubber under the D-Pad is worn out, which I then give it a lower opinion.
NES: One of the controllers that I had was a HORRIBLE D-Pad. It was soooo stiff and my thumbs hurt after playing maybe only 3 minutes. The two controllers I have now are much better. One of them is actually quite good, but another one is actually a bit loose.
SNES: The rubber on these is quite worn, so I really don't care for these. I will replace them one day, and maybe I will talk about what I think of them with the replacement.
Super Famicom: One is like the SNES, but another is in a slightly better condition.
N64: These honestly don't press down enough for me to like them.
GameCube: It's a little bit better than the N64, but what is it?
Wii: Actually it's not bad, but I wish it pressed in just a tiny bit more.
WiiU: It could be better, but it could be a lot worse.
Switch (Lite): It's also not bad, but I wish it pushed down even more than I wish the Wii pushed down.
Master System: Honestly, I like this one, even though it honestly is not the best one to use.
Genesis (3-Button): No not really, but it could be worse.
Genesis (Retro-Bit 6-Button SEGA-Licensed): This one is quite nice.
Mega Drive (3Button): No but it could be worse.
Saturn (Original): No, but apparently, don't people like the roll on this one?
Saturn (Retro-Bit SEGA-Licensed): This one is better, but I actually don't care for the roll on the Saturn D-Pads.
Dreamcast: I want to like this one. I actually kind of like the roll on this one, but I wish it felt more like a button instead of pushing into a kind of thin blanket with something solid underneath.
GameGear: Please no.
PS1 (No DualShock): I have 3 of these, 2 of which I had easily accessible while I was writing this. Those two were not terrible, but I wish they pressed down more.
PS1 (DualShock): There are some things to like but also there are some things to dislike about this one.
PS2: These are quite nice, but this is a bit unrelated, I don't like the pressure sensitive part of the controller.
PSP: Eh.
SNES Classic: If this is what SNES/Super Famicom controllers originally felt like, I wish they pressed down more, but they are definitely better than the original controllers I have. No wait I just pressed down after writing all the rest of the bullet points and dang they are stiff.
Genesis Mini: These are quite good. Like the Wii, I wish they pressed down a tiny bit more, but no these are very good.
GameBoy: My Grey one is very worn, but the Black one is in better condition. They are not my favorite, but if the Black one is what it is supposed to feel like, it is not bad.
GameBoy Pocket: I don't like the roll.
GameBoy Color: I don't know what to think of this one, partly because I switched out some of the D-Pad hardware in the one I have. It's maybe average.
GameBoy Advance: I wish it felt more like a button but it's not bad.
GameBoy Advance SP: It's all right.
DS Lite: This was my first ever game system. Because of this, the D-Pad rubber is actually torn, and I need to replace it. I remember it being fine, but this was my only system for a while.
3DS: I am not a fan of the tiny clicky keys at all, but on a D-Pad, it kind of works.
New 3DS: This is the same as the 3DS, but maybe I like this one a bit more.
WonderSwan: There is no actual D-Pad on this. It is just 4 separate buttons.
WonderSwan Color: Based on what I just said, what do you think I would have written here?
Ok, and now my favorite is:
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...actually I think it's the Genesis Mini D-Pad, and then maybe the Wii, oh and the RetroBit 6-Button. Honestly the D-Pads I actually hate using are maybe the GameBoy (my grey one) and way above that all of the SEGA 3-Buttons I have, though I can use these without much problems, and some are definitely better than others. One of my Genesis ones is just stiff, while the Mega Drive is not as stiff but I wish it pressed down more. Except for maybe the grey GameBoy that I have, I actually don't hate any of them.
January 21, 2021
Since I now have a PC Engine, I can talk about the D-Pad on specifically the controller model PI-PD6. It's not the best, but it has a decent travel downwards. It's quite useable.