Survivorship bias is heavily affecting your views on what previous era housing actually looked like. For example:
"they'd also likely be appalled by the level of maintenance required to maintain"
Modern materials have much lower maintenance requirements. You can put up a tar-asphalt roof and aluminum/vinyl siding and be fine for multiple decades without needing any maintenance whatsoever. Meanwhile, a lot of older houses needed extensive maintenance every year to keep the roofs and walls in passable shape. Wattle and daub was a common material used for walls, for example, and thatch a common material for roofs. Both are incredibly labor intensive to maintain.
"With that taken into account, we spend a good deal more of our lives providing ourselves with shelter."
Huh? How are you measuring this? The average person centuries ago lived at just barely subsistence level. They spent most of their efforts on basic survival, and sometimes didn't even have enough to eat. We spend much less of our lives laboring now than our ancestors used to. Compare how hard and long a subsistence farmer or serf works vs a modern office worker. It's much easier for us to provide shelter; we just spend some fraction of our salary on it.
"home of five hundred years ago was likely built with the most durable materials that were feasible for the time and budget"
Yeah, so only the palaces were built amazingly well and everything else was not. The living standards were so much lower back then that almost no one had the money to get access to the best available stuff, whereas nowadays most people do.
"a home with a beautiful bay window is a thrown rock away from being essentially uninhabitable until that window is replaced"
I don't even understand this criticism. The only way to not have this be a problem is to literally not have glass windows at all. Either you have an empty hole in your wall that's terrible for retaining warmth in cold weather and keeping out bugs and rain, or you don't have holes in your walls at all and live in darkness (both were common options). Would you seriously rather live in a house without windows??? To the extent that people didn't used to, it was only because glass was so expensive that the average person couldn't afford it. Now that we have modern production methods, glass is cheap, and everyone can benefit from it. I guarantee you that if you went back in time offering free glass, the average person would gleefully put it in their house. It was only used in palaces, cathedrals, and the like because of how expensive it was.
The average person 500 years ago lived in what you would call nowadays a ramshackle hut. I don't know what is coming into your mind, but you're probably thinking of one of the few well-made structures that persists to this day, rather than what was actually commonplace. Keep in mind that entire cities used to burn down too, which no longer happens in good part because of modern fireproofing codes and materials. Drywall, for instance, is an amazing material.