It sounds like 1) could've been partially avoided by going with an RPM-based distro.
4) and 5) would've been problematic on Windows, too (in fact, Windows would've struggled even more with 4).
Hopefully 2, 3, and the remainder of 1 will continue to improve, but they are indeed obstacles even today (users tend to get frustrated with Linux's "quirks", and the driver situation is still abysmal for printers and scanners, which are vital in offices; Wine is getting good enough to be a viable solution in some situations, but it's by no means a universal solution at this point).
4) and 5) would've been problematic on Windows, too (in fact, Windows would've struggled even more with 4).
Hopefully 2, 3, and the remainder of 1 will continue to improve, but they are indeed obstacles even today (users tend to get frustrated with Linux's "quirks", and the driver situation is still abysmal for printers and scanners, which are vital in offices; Wine is getting good enough to be a viable solution in some situations, but it's by no means a universal solution at this point).