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When did you start feeling hms were a liability/outdated?

Defog. Why. Who thought that was necessary in any way, shape or form.

But, on a more practical way, the moment the games decided that adding random dancers to block paths was an acceptable roadblock. That very second, HMs died. And in a game choke full of arbitrary HM barriers like DPPt, the blackout guy in Verity Lakefront was a harbringer.
 
Defog and Rock Climb. I started on Emerald so never took much issue with the abundance of Water HMs (Dive is cool too), although I kinda figured a Pokémon tough enough to carry me across the open sea should be able to carry me up a waterfall with the same skill? Then again, perhaps water routes are actually rather shallow, with the rocks breaking a lot of the waves?
But Defog - although optional - seemed absurd, as I figured Pokémon were fighting in such close quarters only a fog thick enough you couldn't see the screen would cause an accuracy drop. Rock Climb has grown on me, but as I'd scaled mountains in Hoenn I found it very frustrating.
Really, the ideal number is 6. 1 per team member. So like the majority of people, it was the games with 8 of them that did it for me.
 
I started resenting HMs as soon as in Gen II when I needed to backtrack to Olivine city and find a pokémon who could learn freaking Whirlpool.
 
I find them to be the most annoying in gen 2 and gen 4. For myself the major problem was useless and/or weak hms in battle. As well as hms that are all the same type. Flash, defog, cut, whirlpool, and rock smash are trash moves that I don't want to waste on my party. Having three water hms in both gen 2 and gen 3 is an annoyance for reasons already mentioned in this thread. I think defog is what really made me over them as a whole.
 
unpopular opinion: i m pro hms tbh. I think the truth is that pokemon games changed. I loved how hms were used in gen 3 and especially in gen4. Then, let's be honest, some hms aren't even so bad as moves. Surf, Fly, Waterfall are really good moves. Strength too is not too bad, especially if u consider that after all it's a pokemon game and the main story isn't too hard. I liked the fact that u had to teach hms to ur pokemon party, it just added a small layer of difficulty that wasn't too bad. I don't think hms are outdated. I think modern pokemon games aren't elaborate enough to use them properly. I think gen6 was the gen when i was like "what's the point of hms, the path is just too easy". Indeed, from gen 6 the "exploration" part in pokemon games went missing and that's imo a very bad thing. I actually think that GF could work on the exploration part tho. For example, I liked the Armor Island part and Crown Tundra. Armor Island was small, but every area can be accessed by every place and at first it's kinda easy to get lost. Even some cave in Crown Tundra was not too bad. Using the 3D to make u feel a bit disoriented at first. That could be good in place of hms, even tho imo hms aren't outdated. They could be implemented in the game in a different way. it was stupid btw removing the traditional hms systed from BDSP. But it wouldn't be the first thing messed up in that game lol
 
I agree with you, piplup! the thing with me is it makes you plan your team better - can't just have 6 dragonites. throwing HMs onto teammates isn't annoying if you plan it accordingly. to be fair, I use several HMs in battle during nuzlockes because they have nice accuracy!
 
throwing HMs onto teammates isn't annoying if you plan it accordingly.

Maybe, but who wants to be conditioned by HMs when planning a team? Even if a couple of HMs can be useful battle moves, it's not allways the case. What if you don't want a Water type on your team?, or what if you want a physical Water type, rendering Surf useless on it? I mean, unless you intend to have a mixed attacker Water type, which seems unlikely, either Surf or Waterfall are going to be useless. And non-Water types that can make good use of Surf are rare exceptions, such as Heliolisk or Dragalge.
 

People generally don't mind Surf or Strength, it's usually something like Cut, Rock Smash, Defog, Flash or Whirlpool that people consider annoying. I do think that with the free and widely available Move Deleter / Move Reminder we see in Gen VIII, those HMs would be less annoying though, since the real problem with them is that they have a tendency to linger on your movesets long after they've stopped being useful.

People also generally don't complain about the exploration when they're talking about HMs (although some people do complain about that), to the point that the people that complain about HMs usually like the way Alola did them, or the way some hacks do them (Key Items). You can have elaborate maps with branching structures and what not without having HMs.

And they just ... feel artificial. There's no particular reason a Meowth should need to know Cut to be able to cut things or a Pidgeot should need to know Fly to Fly somewhere.

Personally I think that an alternative to the HM system that is tonally consistent with the series would be to go for a Rangers-esque style in that any Pokémon that could conceivably do the HM can do it, although how much it can do is decided by some lore details (e.g.: Rampardos can absolutely wreck the biggest boulders you've ever seen, while something like Rockruff can only break small rocks).

That would keep the planning aspect in some forms (although it's still a bit restrictive in that it doesn't make any team you want viable. For example, if I want to beat the game with a Wurmple, a Caterpie and a Weedle, I should be able to do so), make tonal sense, encourage catching and team rotativity in a natural way and allow for more open world exploration and many ways to solve problems (e.g.: a Pokemon might be able to fly you over a bush instead of you needing to cut it).

I also have yet to see a convincing argument why Fly shouldn't be available from the start of the game. It's just fast travel to places you've already been. More often than not doing the backtracking "by foot" is not even hard, just annoying and time consuming, and from a design perspective you should want players to be able to backtrack and explore previous areas after they figured out that hey, maybe they do want something that was around there.

Edit:

agravedigger said:
the thing with me is it makes you plan your team better - can't just have 6 dragonites.

Something I noticed is that, ironically enough, you can. In Gold / Silver and HeartGold / SoulSilver you get access to Dratini, Ditto and the Day Care at the same, just before the 3rd gym.

There are 5 necessary HMs to beat the game, of which only 1 can't be learned by Dragonite ... which is Cut and you only need to use it in one place in the entire game: Ilex Forest, to get to Goldenrod, which is where you get the Dratinis.

Even if you got a Dratini in via trading or something, you only need to catch one Oddish or Paras (both found in the forest) to get to Goldenrod and then bob's your uncle.

Similar arguments can be made to most other games if you just trade in a female Dratini early on / Time Capsule your Dratinis at an early level.

Not that it would even be as easy as you're suggesting since it takes forever to level up one Dratini let alone 6 all the way to Dragonite. You'd probably have an uphill battle most games until you beat the 8th gym or something.
 
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