David,
The information will come across from your customers. One issue is that the passwords won't transfer correctly. Customers would need to reset their passwords.
I've run into some issues with "bad artifacts" being brought over from Cloud. In particular, I've had issues with avatars not transferring and icons not being pulled in.
Workflows have given me some trouble in the past. In Jira cloud, some functionality is included by default, but on server, you need to purchase an add on to get it (Jira suite utilities). This can lead to workflows not functioning as expected, including tickets being stuck in certain statuses until the workflow is fixed.
I've also encountered frustrations with having additional resolutions brought in, old email handlers/service desk email configurations.
One last thing is that whoever the user was that set up the cloud environment will be called "Admin" in server. All their history will be tied to that user. You'll likely need to rename them when you restore to server.
The migration will do a lot of the work for you, but you'll need to watch out for some of those items.
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