First, merge all your separate JIRA Server instances into one - see https://confluence.atlassian.com/jirakb/how-to-merge-jira-applications-instances-244352137.html
Then migrate the result to Cloud - see https://confluence.atlassian.com/jirakb/migrating-from-jira-server-to-jira-cloud-779160826.html
Pretty much the same. Export from Cloud, get that loaded into the latest version of Server, then merge in all the other server systems (this is not usually a "fun" job, I'm doing it for a client at the moment, and it's really finnicky. You'll find it easier due to some bug fixes in JIRA 7)
I have multiple projects that use variations of the same base workflow. The variations depend on the requirements of the project or issue type. The variations mostly come in the form of new statuses ...
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