I'll say it upfront, I'm looking for confirmation that it's a good idea to move a client to the cloud. Now I'll make my case:

I recently took on a new client. It's a non-profit organization with an unusual structure. They have a small office in Maryland where a few people work, but the rest of the dozen employees are all remote, including the president who lives in the mid-west US.

The organization currently uses their server for a single thing: files. Each user has a shared drive and their own private user folder, accessed via remote desktop.

To be honest, the server is also handling user accounts, and is then synced through Azure to Office 365, which is what they use for all their email. So they're already in the cloud.

The client specifically requested moving their files to the cloud. They have a terrible internet connection in their office, making remote sessions very slow. They've also had repeated infections on this server (not sure what the previous IT folks were doing for security but it wasn't working).

It looks to me that Sharepoint in their Office 365 account would be the better option for these folks. What say you folks?

Also, I'm having trouble seeing much of a reason for these folks to have a domain at all, but that's probably my bias showing. These are all remote workers, they're all permitted to install whatever they want onto their company laptops, and there doesn't seem to be any reason to have this server in use at all anymore. As a non-profit I think they also want to minimize IT support costs and a server increases those.

Anyway, I'll accept your opinions, but I'm hoping you'll agree that the cloud is the best option. I just don't know if there's something I'm not thinking of.