However I do find bootstrapping yourself a web app is way easier today than say, 10 years ago. The tools are efficient and a pleasure to work with. Frameworks increasingly abstract out many pains so you can focus on your problem (e.g. Meteor). You might have to spend a few days getting a hang of all the different options before committing to one of them, but once you're set, you can get up and running really quickly.
But at the same time understanding the web itself has become much harder. CSS3 / html5 / ECMAscript 5.1 / JS 1.85 (I looked them up, I can't remember any real fundamental JS changes that have happened recently since they added let) are all much more complex standards. I mean, the number of tags in html5 was increased by, like, 50%?.
Sure, at least now the standards are much more stable than in the 90s (I can't imagine trying to keep up with the rapid and constant platform lock in gotchas between netscape and ie...) but learning all that stuff takes a lot longer.
It is like how you can start a car easier today than you could in 1920. The car is much more complex, but the abstractions built on top of that have made it as easy as turning a key rather than having to rev the engine, crank it up, etc. But anyone trying to be an automechanic is expected to know the fine grained details of the modern combustion engine and all the quirks auto manufacturers use to make them more efficient and performant, or else they don't come off as "professional".
I feel the same way with any development role. It doesn't feel professional if I don't know the whole stack behind it. And the stack, like the car, has only gotten taller. Average Joe can pick up Drupal or jquery + bootstrap + rails and crank out a pretty neat web app, but the second their tools don't cover some use case and they are forced to look at things like the TCP stack, packet headers, http headers, etc, and they look lost, they also look bad at what they are doing.
So as I understand your point is that it's more difficult to get down to 'hacking level' today, thought it is surely easier to glue things together without deeper understanding. Whereas back in the 80s hacking level wasn't so far from day-to-day development. I agree, I hit these roadblocks every now and then and at each point I'm confronted with the deeper question of whether I want to devote time to really grasp what's behind the magic, or is it better to clutch at workarounds so I can turn up an app faster. I guess in the long term achieving hacker level has better payoff, but I seldom take the metaphorical leap.