IME, most characters have a fair amount of skills at low level. However, default level-based DCs go up faster than the 1/level you get just by leveling up, so you need to sink more resources into your skills in order to keep up. But that's when you start feeling starved for skills, as most characters only get a total of nine skill increases. The classes that feel this the most are the ones that are traditionally semi-skilled, like bards or rangers. These classes often have very strong incentives to increase certain skills (Occultism and Performance for bards, Nature and Survival for rangers), which leaves little room to play around in.I also am a little puzzled by someone feeling PF2e characters are skill-starved; maybe this is a consequences of playing a Fighter and a Champion, when 3e era D&D was notorious stingy with skills for Fighters and Paladins, but I felt I had a pretty reasonable number of skills there (partly, as you say, because picking up one along the way doesn't turn into an exercise in futility). Its possible that could feel that way for things like a Wizard who got a lot of skill points because of Int in earlier versions, but I'm kind of hard pressed to see it with any of the others.
You also have some skills which tend to be tested against harder things than others. Stealth usually uses an opponent's Perception to set the DC, and a monster's Perception goes up even faster than normal level-based skill DCs. Thievery is often used on locks and traps, and they have horrendously high DCs to the point where if you're not maxed out with both skill ranks, stats, and gear, you might as well not bother.
I think it's because once you get some automation, you start expecting more. I mean, the VTT knows that when I click Reflex on my character sheet, it is supposed to roll d20+the number it has calculated. But then it ought to know that I'm Clumsy 2 as well which should give me -2, ought it not?It goes even beyond that though; a lot of people clearly expect a VTT to automate some elements of resolution, but no one asks why that's mandatory there, but you can do otherwise face to face.
I mean, I get some issues; having a die roller utility built in can at least be really desirable when playing with strangers, or for people who really like to see the die rolls as GMs.
But, while convenient, why does the VTT have to track hit points, monitor conditions, and all that? We get by fine without it face to face. But some people seem to take it as a given the VTT will do that or its unusable.
I think it's also because the act of writing down a condition or similar thing IRL aids in remembering it, but just adding it in a VTT doesn't have the same tactile memory quality to it. There's something about having to think about a thing enough to write it down that fixes it in your memory.