Of the four boxes I have in use three won't run under Linux. Two because a key hardware component has no stable/usable driver support (Wacom penable digitizer) and two because the graphics card is not supported (one is the add-on card in the penable the other the card in an AMD E-series based Compaq/HP). The latter was tested recently (late 2012) with the then current Suse since I prefer that over xBuntu.
So my choice would be "run two different OS" (Susie on the tower and Win8 on the penables/mini). Not going to happen, even less so since Windows is set in my work environment anyway. I even sold an Android tablet. It was light and had good endurance (On par with the T731 for 1/3 the weight) but was an "alien" in al other departments
The "reboot after updates" is no problem on a workstation. I schedule updates for "when system is shut down" and that happens daily. No need to keep a client running when not in use. Servers are another thing. OTOH on privat servers I prefer Solaris for it's long term stability
Installing Win7 or Win8 was easy, cards where detected, drivers where found in Windows and then updated automatically. Last time I had to search lengthyly for updates was in the days of XP.
And that is all before I come to the needed software that simply does not exist on Linux. No equivalents to MS Journal, OneNote (No, EverNote is not since it is a cloud solution), ArtRage, Handwriting recognition, Speech recognition (Yes, I use that a lot)...
(1) Graphics card is optional there / base driver is enough