I would say biggest issue with licensing comes from clear attribution being problematic at the scale of OSM not the virality or relicensing problems. That and OSM aiming for being squeaky clean, far away from any ambiguity in terms of third party data licensing.
It is simply impractical to attribute all the sources anywhere in UI or printed copies of map. And whether an attribution hidden somewhere deep in wiki is considered acceptable is grey zone.
The fact that OSM themselves want attributions is another reasons why they have high standards for what's considered an attribution which they can't achieve for third party data sources.
In case of software License.txt and Help/About is considered standard practices. But that doesn't necessarily translate to other mediums of copyrighted work. Something like books or research papers have their own generally accepted practices of how attributions are handled. For maps digital and physical text in the corner is often used practice. You can see it even for something like a building plan posted next to construction site, listing additional map sources used for preparing the drawing. So it's not exactly unique invention by OSM. Back to comparison with software, software can't exactly be printed out so the concerns about attribution are different. Also software licenses typically require listing including a copy of license text not just attribution , which is simply impossible outside separate file or dedicated UI.
In practice the OSM aiming for better than good and thousands of unverified contributors being uncontrollable lands it somewhere in the middle. But if they aimed for barely acceptable all the contributors would definitely push the bar bellow legally acceptable.
On the topic of government data, CC-BY is also common which is somewhat problematic. But more often they have no idea under what license they are releasing their data. They come up with complicated schemes of metadata, which never gets properly filled or parsed, thus resulting in conflicting information about license being used. And if you ask them to clarify they will just say, "yes yes it's open data you can reuse it", with the government employee having no understanding about differences between various licenses and that not all open data is equal.