Looks like someone made a tutorial specific to tomb engine and wine: here Doesn’t look super complicated compared to some other windows only applications I’ve been tasked with getting working, (I’m looking at you proprietary Harley Davidson software my father in law was struggling with).

It boils down to a) install wine, b) install winetricks c) install tomb engine, d) use winetricks to fix a dll.

You’re right though; Native wine isn’t particularly noob friendly.

Alternatively you could try bottles (basically wine with a better GUI) or just install your application using native wine, then add it to steam as a non-steam application and enable proton compatibility (this works surprisingly often with no extra config weirdness).

It’s actually quite simple to determine who an organization uses for their mail and data. All you need to do is review a domains DNS records (using a tool like dnschecker.org) and look at the MX record.

For Microsoft/office365, you’ll see some variation of “protection.outlook.com”/“exchange.domain.com”. For google, you’ll see a variation of " MX.google.com".

DNS records are public information. The two biggest players in the space are Microsoft and google, the majority of SMBs do not host their own mail servers.