Neither of us have any experience with the cloud, whereas we have a lot of Microsoft experience. We still rely on OEM licenses of Office, because Office 365 would be 3x or more expensive. We have a range of Office 2019, 2016, 2013 OEM, and we get audited by them nearly every year.
We use LastPass, Dropbox and Github, but only the basic features, and LastPass was an addition last year after someone got into our network through a weak username/password.
In our main location, we have three ESX boxes, running several virtual servers, and then we have a physical server for our domain controller, file sharing and DHCP, DNS in other locations. We also switched to a physical server for our new ERP application server, which hasn't yet been rolled out.
Projects like upgrading our ERP version can take months, but we have a local consulting team, with a specialist in our particular ERP solution, as well as a Server and Network specialist, and we also have a very close relationship with our ISP, who provides WAN troubleshooting.
Our IT budget is small relative to our company revenue, so most cloud proposals would raise our costs manyfold. We continue to use more services like Github and Lastpass, and we both have multiple hats.
I'm a developer, in-house app support, Email support, HR systems support, ERP support, PC setup, and I run our Data Synchronization operation and my boss runs EDI. I do a lot of PowerShell and Task Scheduler, but I've got familiar with bash through git bash.