IE wasn't awful at the time it was built. It was ahead of its time in some areas. It became awful because of tech debt: people building for it and only it. Companies having key line of business apps built solely for IE that locked everyone into a compatibility nightmare.
It is the same thing with the "Just install Chrome" crowd. If all anyone uses is Chrome, then no one else can move forward without first guaranteeing "Chrome compatibility" rather than spec compatibility. How soon until even Chrome has to maintain compatibility with ancient Chrome bugs because some Fortune 500 company relies on that specific bug for LOB software, willing to throw money at dumb bugs? (That Fortune 500 company could even be Google at this point, because they very much seem to have invested in an internal monoculture.)
(Your Mac coworkers can find free Edge testing VMs from Microsoft. There's also "headless" tools like BrowserStack.)
Too late. This has already been happening for years in the mobile space. It's why WebKit refuses to remove -webkit prefixes, and other browsers are now forced to implement them.
I don't think this has much to do with Chrome - I suspect the iPhone's dominance of the mobile browser share is a big factor.
The web has a long history of post-facto standardization where implementation comes before standardazation (see browser wars).
To this day, the versions of IE in use by actual people are awful. MS finally has Edge, which isn't awful, but absolutely no one uses it.
If I tell an end user to get Chrome or Firefox, that's the end of the problem, whatever system they have it will work. If I try to tell someone to update their IE or to get Edge, I'm stepping into a black hole of trying to divine which version of Windows they're on and how recent their updates are. None of my mac loving coworkers can easily test against IE or Edge and headless unit testing against IE isn't a thing.