Eyes on the prize, captain. If they're using a cloud-based EHR, that means that the HIPAA responsibility is theirs, not yours. If you've got an encryption handshake on your side you are donezo.
We've got two EHRs and a Synology. All three are encrypted. The Synology is a lot less touchy-feely; both of the EHRs can be hit with an iPad through a web browser. And look at it this way: HIPAA violations are a problem primarily from a litigation standpoint. If someone leaks your diabetes status it's not the end of the world for anybody but if the government catches you doing it it's what? $50k? Thus, the mad rush to cloud-based EHRs where single practitioners can hand it off without having to worry about it. I've had this conversation maybe a half dozen times and for any organization small enough that Siemens isn't hand-writing patches for you, the cloud-based stuff is plenty good in my opinion. You are welcome to convince me otherwise.
A similar philosophy can be applied to Microsoft. I didn't full get their 365 thing until I got to a university; I give it my login and it populates my desktop, my documents, my onedrive and my preferences (and some drivers; it's fuckin' insane). I log out and it blips all that shit. Microsoft is effectively turning the whole world into dumb terminals that happen to run Windows. And to do that, it's an enterprise environment with a staff of MCSEs keeping things humming.
These are the guys that are going to pay Enterprise, or heavily-discounted Enterprise, or whatever it takes so they can do what they used to do with Ghost only faster and better. And these are the organizations that Microsoft can audit and have it be worthwhile; no more swooping in to nickel'n'dime operations and checking licenses. If you've got a thousand seats they've got a good idea of where you're at.
Win10 Pro then just becomes the thing that SOHO uses so they can put off updates until it isn't going to kill their business.
It's not your money. Take a back seat. Say "yep, we're buying these packaged solutions now because the operation of our business is being centralized in someone else's silo. And we can fight the flow and I become your key man who holds your org on my shoulders like Atlas, or we can jump in the river with everyone else and all drown together."