Atlassian has pretty good documentation on this, actually. The easiest way to find what you are after is with Google, actually (I don't mean it sarcastically.) If you search for "jira 7.6 supported platforms" rather than "jira supported platforms" you will find things that pertain to your exact situation. Atlassian has also made it easier by adding the version dropdowns on many of the docs.
Back to your questions, though. Check out the Crowd upgrade docs. Additionally, check out the Supported Platforms page for the version you intend to run ( 3.4 ) to make sure you install a supported Java and run a supported database version. Depending on the database choice that you made back then, you may need to factor a database version upgrade in to your plans.
Here is my thinking on what version to upgrade to. Ultimately, you will need to decide what is best for your situation, though. You are faced with 3 options. Each have benefits and drawbacks. My analysis of the three options:
1. Latest and greatest.
Benefits - You have the new hotness. All the latest features are here. Atlassian EOLs (end of life) their products 2 years from release, so you have the longest amount of time before EOL. No one will complain about being on an old version.
Drawbacks - The pool of people running the latest version os fewer, and there is a greater chance that you may encounter a bug. You're only on the latest and greatest for a few weeks until the next release comes out. Some App vendors don't release their products as timely as Atlassian's releases, so some Apps may not be available for the latest version.
2. Arbitrarily selected earlier release.
Benefits - Possibly greater stability, since more people are running this version. Good likelihood that your Apps will have a version available. More features than you have now.
Drawbacks - Bugs in this version might have been fixed in a later release.Your users will question why you went to the effort of upgrading and didn't go to the latest version. EOL comes sooner.
3. Enterprise release.
Benefits - Version has been vetted extensively for stability and security before being declared "enterprise." Atlassian back ports patches to address stability and vulnerabilities. If a vuln is announced, you simply update your version to the latest release and don't need to go through the functional and App testing you would in a normal version upgrade. No extra cost. Same 2 year EOL policy.
Drawbacks - You are always on an older version. Enterprise releases are declared 1 or 2 times per year
I hope that helps
![Dave Theodore [Coyote Creek Consulting]](https://avatar-management--avatars.us-west-2.prod.public.atl-paas.net/557058:a1f94001-e8c1-4ab0-95d3-01a204687231/254ecf19-a9ab-40df-9b8a-51a3251ea418/128 "Dave Theodore [Coyote Creek Consulting]"){kind=avatar}
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