First off, getting cast in the deep end like that... good luck. However, I am sure you'll win out. I went through similar not long ago (not as huge of a leap as you have) going from JIRA 6.0.x to 6.4.x. That, in itself was painful enough.
I think your first step would be to review all the release notes (here) between your version and the upgrade guides (also as other pages in this link). That'll at least give you a roadmap to follow.
Another suggestion I might make is to just build yourself a new target server totally for this and use that both as your dev server to get from A to B and when you do it successfully and it's clean, just flip the DNS. Given the age your version of JIRA is, it's also even money that all the platform bits (OS, DB, etc) are equally out of date. Pay special attention (also contained in that same tree I put the link in for) to the platform requirements. I can highly recommend running this on either Linux (your choice; just pick a light fast one) and PostgreSQL (all my Atlassian tools are on this now; one of our other divisions is running the same versions as I am on MySQL and it is significantly slower than mine).
When I made the largish leap on JIRA, I worked out the roadmap and then trial ran a migration to the new platform, saw what broke, corrected it, and tried again. Basically when I could successfully, three times in a row make the migration, validate function, and validate data integrity, I called it a successful and viable migration plan that I then did for real on the production system. Even after that, I kept the OLD one running for a couple of weeks in case something didn't make the leap so I could go find the data/function/whatever and replicate it in some way to the new one. If your instance isn't too big, I can highly recommend the XML backup/data directory copy method. That was what got me there eventually (with tweaks to solve the other things cited)
You'll want to pay a LOT of attention to plugins to make sure that what you are running either has a new version for where you are headed and, if there are groovy scripts in there, either get them fixed to work with the new java classes and APIs or, better, stomp out the functionality and redo it with plugins that do the same thing but then become a SEP (Someone Else's Problem) to keep up with the changes in JIRA (the developers of the plugins)
Hope this was at all helpful in some way
Thanks for the info. I'm reading through the "upgrading JIRA with a fallback method" guide now.
Since this is on a hyper-v Windows 2008R2 machine, I think my plan of attack is to clone the VM, install the next versions and configure through the steps and such, and then turn off the old server. I have to juggle the current server at the moment because it's actively used, but once I get a moment to take a clone, I'll have something I can play with.
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