As someone who has never raised a single Pokémon above Lv15, I can say with confidence that Lv30 isnt a necessity, especially given that the diminishing returns from Lv20 to Lv30 are really big; the high BP Pokémon only gain +15 AP, though the Kanto Starters get +20 AP for whatever reason. Definitely not worth it folks.
As someone going through the main stages (any% itemless) at the moment, I can say with confidence that the new mains are a lot rougher than even Nacht Carnival. Currently up to Salamence (610) and beating that itemless (Which is what you need to do if you want to PSB farm it) is pretty much predicated on you having Mega Beedrill, perfect Alolan Ninetales, and perfect LDE Regirock (or a perfect Hyper Bolt Capchu) with good RNG. I don't have perfect Regirock (only SL3) so I am struggling, but it's a challenge that I want to conquer. 8 moves, five figure sum HP, and disruptions affect top two rows (barriers + blocks). It's not exactly something I would call doable itemless if you are playing casually though.
And that's not the only annoying stage in the first 10; Cryogonal is barrier hell which mandates Mega Diancie and has a ton of HP, Kricketune has really annoying disruptions, Basculin-B loves its blocks and Basculin-B (and they cover the middle of the starting board) and that's only 10 moves, Snover is three-mon but has a bad starting board and forces you to bring Snover, and so on. And that's only the first 10 stages. Itemless progression (especially for PSB Farming) is basically an LDE-fest.
Then again, this is Stage 601+ we are talking about, not Stage 301+. For casual players though, these stages are kinda really hard.
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That said, I kinda have mixed feelings on this update. I like that they buff things to keep it fresh (Gligar buff!!!), but what I don't like is that they are inevitably going to force us to invest in these things in order to do any of the new content. I mean, if they are going to make things really challenging and make it so you need a specific buffed Pokémon to win, they should honestly keep it to the back end of Escalation Battles (and strictly the back end) to keep them challenging even for veterans and stop them from being borefests. Don't make it really difficult to catch Pokémon (without spending coins) without a specific buffed Pokémon (Hi Rapidash, Hi Tapu Koko) otherwise casuals won't have much of a chance. Competitions I don't really care about (I just do one and done runs nowadays), but don't make the main aim of this game (To catch 'em all) increasingly "gated" just to keep things challenging for veterans with their buffed everything.
But GS being GS, I can't help but to feel that in a few week's time, there will be a challenge that will pretty much rely on you having Lv30 SL5 Try Hard Snorlax (Which deals 25× DMG at SL5) to win without paying up a lot of coins... Oh wait, that already exists in the form of Survival Mode 2.0 (hi 2/3 chance of getting Snorlax on stages 58/59).
I think being "late game" doesn't necessitate stages like this
As you have kind of poitned out, even for veterans, the stages can be total crap shoots to beat much less s rank. Even with huge damage dealers, so many stages have so much HP to burn through. Even all item runs are starting to get more luck based without investment. The game can't grow in difficulty forever....where does it go from here? It's so short sighted.
And I think the thing on top of all this, is in the insane resource management. Especially these days, the only real source of RMLs is placing very high in competitions that are getting increasingly luck based and Escalations that are huge time and money sinks. And both of these are having their already existing issues exacerbated. Competitions often require a flavor of the week pokemon at max RML level (at least 5) and max skill level and likely a skill swapper and there's no guarantee that pokemon becomes useful any time soon. Escalations are long affairs, sometimes require their OWN flavor of the week, and to get the msot out of them you usally want to go to the end which can be 400-500 stages depending!
But even then, the resources you get seem so scarce. You get what, 5 RMLs out of an escalation if you go through it to completion? But they keep adding more and more pokemon, likely useful ones, who require RMLs. And some might genuinely want all
10. We'll ignore the ones that can now take 20 (which screw off gs). And then on top of THAT you have to grind them up which is just.............we still only have Ampharos during the week. 50 exp, 100 if you get a crown on a long tedious stage. IF you got the crown on the pokemon you wanted every single go, it would still take 20 runs to go a single level in the latter RMLs and I can't imagine what that's like at even higher levels. There's Victini/Magearna but you get 1 shot at them a week, and even with a jewel it's only one more shot
meanwhile exp boosters are still rare? And then they dont give that much....they give out smalls the most but woo-hoo ~50 exp~. I think M gives 200. Larges are ultra rare. Full level ups are realms of competitions. Survival Mode used to be the best for the smalls, but even that always had me give it a side eye considering the time and effort needed to beat it (which is the only way to really break even iirc). But that's irrelevant now any way since it got buffed.
AND they keep making terrible terrible pokemon that suddenly become useful & good but onl after max investment.
Not every pokemon gets a grindable stage for PSBs and the ones that do often get either limited time frames or are a money sink due to RNG; and on top of that grinding for those skills may become super outdated later. There is Eevee at least, but even with jewels that's not too many skill boosters per week.
This turned into a long ramble, but god, what do they even plan to do with this game. I'd say how can newcomers even hope to keep up...but do they even really care so long as they can put a squeeze on th whales? We've seen those competition numbers, it ain't good. Or the plethora of "great" challenges.