we are currently using JIRA (100 licence, Server) and thinking about integrating Bitbucket.
Yes, it is possible to integrate JIRA Server with Bitbucket. The integration works by installing a post commit hook into bitbucket. This hook fires a message to JIRA and requires your JIRA server to be able to receive traffic from the general internet for all the functionality to work. Docs: https://confluence.atlassian.com/display/BITBUCKET/Linking+Bitbucket+and+GitHub+accounts+to+JIRA
On licensing you don't need the user tiers between the products to match.
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