If I make a mistake, somewhere, and have cloned 50 rigs off that, and later I find out I messed up, that is a 50x mistake multiplier I'm not prepared to risk. You can mess up just as easily by something you don't do.
With single install, I'm isolating risk, constraining it to THAT rig.`
IMO your logic is flawed: Obviously the more actions you take the more chances you've got to fuck up.
Do it ONCE proper, test, automate deployment, test again.
Also I use this
http://www.winsetupfromusb.com/downloads/ to create multiboot USB with acronis, all needed Win versions, Ubuntu, BootCD, and the actual image. ... and I cloned this USB drive too:) and because I'm lazy and it actually saves tons of time and gets the result I used the same fine tuned win10 miner image for my vaio laptop (and it's way better than the bloated shit it came with)
Note on updates: why would anyone want to update or in fact introduce ANY changes to OS under miner, if it hashes at the rates its GPUs are capable of?