Note for Nowlan Freese: If you have some time to pitch in on this, it would be great.
Mainly we want to know more answers to this question:

• Migrating to Jira cloud and retiring our Jira server - good idea or bad?

Migrating users:

• Atlassian advices us to "assess and prepare your users for migration." See: https://support.atlassian.com/migration/docs/assess-and-prepare-your-users-for-migration

• Jira cloud checks email addresses belonging imported users. It also uses email addresses to uniquely identify users. What is the scope of that email address within the entire cloud?

• How does it handle "inactive" users (shown with lines through their names in the Jira Server Web interface.

• I de-activated a lot of accounts belonging to graduated students and departed employees, but didn't delete the accounts. I want to keep all or most of their content, and know who contributed what. I want to use Jira Cloud "free" version, which limits active user number.

Admin:

• Can I grant admin privileges to other Atlassian accounts without "using up" my Jira Cloud seats?

My wishlist workflow:

• Upgrade our Jira Server to the latest version, keep running it but don't add new content for six months or more after the migration to Jira Cloud
• Migrate to Jira Cloud after the upgrade to the latest version, to take advantage of improvements made to the Migration Assistant (Atlassian's prefered tool for migrating Server to Cloud)
• Use the new Jira Cloud instance for at least six months, then re-assess (it might be terrible, but probably it isn't.)

Jira Server end of support: Feb. 15, 2024
This means no more bug fixes/security updates, but we are running an older version of Jira Server anyway, so how much does this really affect us?

Anonymous Reddit discussion on the pros/cons of Jira Server vs Cloud: https://www.reddit.com/r/jira/comments/moukkh/why_do_some_companies_use_jira_onpremselfhosted/

Blog on pros and cons: https://thejiraguy.com/2020/10/07/whats-the-deal-with-jira-cloud/

Cloud Cons
Security is a big issue (not for us since we are open source). Cost is increased (not sure how it would compare for us). Control your own Jira update schedule. Not as much custom plugins (I don't think we use any?). Need to have a <yoursite>.atlassian.net URL.

Cloud Pros
It should just run with very little management on our part.

From: https://www.reddit.com/r/jira/comments/14wruy6/jira_server_after_feb_2024_could_we_keep_it_as_an/

You will probably end up paying more to keep your vm running than to incur the additional costs of housing this data on cloud. Keep in mind that issues created by issues commented on by departed employees will still be accessible and can be migrated to cloud. What will happen is that your user profiles tied to departed employees don't take up an active user license. You'll still be able to see a JIRA ticket created by an inactive user.

That's not the experience we've seen in early test migrations. We are using Crowd (sic) too. So the migration assistant is seeing all the users from that directory as licensed users despite only a fraction of them being assigned application access in Jira.

So one person saying inactive users don't take up an active account and another user claiming that they do.

It looks like Jira Site Import as of Nov 2023 has been replaced with migrate-data-all-at-once - https://community.atlassian.com/t5/Atlassian-Migration-Program/Streamlining-Data-Migrations-amp-Discontinuing-Site-Import/ba-p/2359542

How much storage space is our Jira using?

Comparing plans: https://www.atlassian.com/software/jira/pricing?tab=cloud

The Standard Plan would cost $850 per year for 10 users, billed annually. It comes with 250GB of storage.

The free plan (up to 10 users) comes with 2GB of storage.

A c5n.large EC2 has an hourly rate of $0.108 which equates to $946.08 annual cost.

Trying to find a recent demo video/walkthrough for migrating
https://www.youtube.com/watch?v=fcom2K4iD5M

Are we using any of the Jira Apps on our current Jira server?

https://marketplace.atlassian.com/addons/app/jiral

UPDATE: It doesn't look like we are using any add-ons.

Application Link: https://wiki.bioviz.org/confluence
DVCS accounts: linked to lorainelab bitbucket

DN explored using migration assistant after upgrading a jira instance to a later version which has this feature. Some problems encountered. AL taking over as she thinks she can do it herself, freeing DN to work on upgrading IGB.
Decided to upgrade our Jira server to latest version and then import data to cloud.
Moving this to backlog while working on upgrading Jira server and confirming that we can restore our jira from backups.

Decided to not do this because we could never get the cloud version to work properly.