As the scale of a program increases, the probability that someone will do something wrong increases polynomially. Consequently, as web sites got larger and larger, the probability that some component would break the XML goes up quickly. This is a difficult pattern to deal with, pushing up the skill floor required, and as HTML5 shows, it isn't even all that necessary.
There was also similar exposure from the data side; as the amount of data you handled increased, the odds that some data would tickle some code path that you didn't even know could blow up went up. You write your news front page in XHTML, and everything seems fine for six months, until someone finally includes an ampersand in their headline, and your entire front page crashes for two hours (not in any way monitoring will pick up, either, so you're getting customer reports), and it takes you hours to discover that someone was passing through the headline (and just the headline!) unencoded.
The problem isn't XHTML's rigidity per se; personally I'm inclined more in that direction myself. The problem is when you have a ton of sloppy systems working together (MySQL, old HTML generation code, plugins from third parties your don't control, open source written by people whose belief in their understanding of HTML exceeds their actual understanding, decade-old internal databases with poor validations and unknown provenance, and so on and so on indefinitely), and then trying to suddenly, at the last minute, couple that big sloppy pile of technology to a strict technology at the last second. That sudden mismatch there at the end was a huge problem.
One of the reasons I tend to prefer being as strict as possible is that in general, starting with existing strict-tech and adding sloppy-tech to it is no big deal; the sloppy tech doesn't complain that it only gets a subset of possible data it will accept. And if you need to couple to strict-tech, you still can. But if you start with a sloppy-tech system and for some reason need to couple it to a strict-tech system... prepare for some long nights and blown deadlines. So, professionally, the correct default is to choose strict-tech whenever possible. But XHTML forced that at almost the worst possible place.