It is easier. If you wanted to create a web application from the dotcom era, you could probably knock it out faster by one or two orders of magnitude. It will probably look neater too, and you won't spend days or months tuning it so it will look decent in IE. We even have amazing CSS capabilities now.

If you wanted to create something that's better than the pages we had in the Geocities era, you can do that in 5 minutes (download some static page generator, add a theme and voila).

When it was unveiled, the GMail frontend was a remarkable feat of engineering. Nowadays? Polishing to that extent (also scaling, etc) will take time, but creating a knockoff UI is no longer a revolutionary job. Most web developers would be able to single-handedly replicate the basic functionality ('ajax' and lots of client side javascript are no longer arcane).

As web development progressed, so did expectations.

well, so if requirements were easier back then you can't really say things got easier. The stack got harder. you used to be able to get by with asp.net / php and that's it. Yes, you would throw files into ftp and there weren't any stackoverflow or frameworks. But still, the amount of knowledge you needed to keep up was way less than what we have today. My point: 20 years ago you could learn php and make good money. Nowadays you can't get by without a convoluted front end stack as well, which kinda doubles the amount of knowledge you need to carry.

You can still do simple stuff, it's not hard: just don't use the complex garbage :)

I wrote a web app the other day with vanilla Python, it doesn't do much (it's a tasks app for my wife and I), but it does it's job, and in one file even! It doesn't use fancy front end stuff, just HTML template strings and some links that send CRUD ops to the server, then that saves the data in a big text file. It uses CSS to make it look nice.

I bet I could get a hundred people using it without edits, and it took a few hours. With a proper database and server, it would support thousands easily.

We all do what our managers / tech leads / architects tell us to do in the end of the day. Even if you have a lot of say where you work, eventually you will join a company with an established stack over which you'll have little control. If you're going to do web development there's zero chance you can keep this up forever unless you're working for yourself. Don't get me wrong, I wish the industry would do more of what you're describing, unfortunately it's just not happening.