They know the answers to all those questions. they just don't have the time or cash to sort it.
I was involved with our local NHS trust doing the windows seven rollout.
All such projects end the same way. A total windows seven rollout turns into a windows 7 rollout in 80% of cases, with 20% being frantically rolled back because applications X,Y and Z don't work any more, critical web based services 1 and 2 don't work properly etc etc.
It's all well intentioned, and it seems simple to those who have done such things in the past. Dealing with a couple of decades of reliance on certain things, decades of bodges and corner cutting and decades of things becoming just bespoke enough to never work again if moved from XP/Vista/Whatever. A few years of "well we stopped paying for support on that" or "Bob got fired and only he knows where thsat is/how that works.
It turns an OS rollout into a nearly impossible task. AFAIK north notts NHS trust is still not fully windows seven, and my contract with them doing the rollout was now over three years ago.
It's alright saying "bin it of it doesn't work" but these are hospitals and GPs (or the rozzers). Doing so means things like Xrays, surgeries and emergency treatments grind to a halt. The reality is you roll back in those cases and then the *new* generation of bodges, work-arounds and corner cutting begins.
All of which means the next lucky few who get to do the next upgrade will face exactly the same issues all over again, only now another 5-10 years has passed.