It's funny you would make a dichotomy between the "old guard" and the "hipsters", and blame the latter for the problems of the new Google Maps. If there's anyone on Earth who I can name as part of the "old guard" of online mapping, it's Bernhard Seefeld, who invented draggable tiled online maps when he launched map.search.ch in 2004. (Google Maps was launched in 2005.) For the last few years he's been working as the product management director for the new Google Maps.
If I had to come up with a reason why the new Google Maps feels worse in many ways, my guess would be second-system syndrome.
IMO it's definitely Second-system syndrome. Maps worked fine and didn't need much added/changed, but someone decided that they needed to keep iterating and now we're stuck with all the cludge built on top of it now.
It wasn't iteration. They threw away code and started from scratch. Things you should never do [1].
Several months ago Google releases totally new version of Google Maps. Google Maps consistently stays as a poor product since then. I think that even first version of Google maps (introduced in 2005) was better.
If I had to come up with a reason why the new Google Maps feels worse in many ways, my guess would be second-system syndrome.