I'm counting your voices!
Let me know, who has already decided to switch from Server and who is still waiting (and why?).
I have recommended my old company to stay on Server for as long as possible. The price of Data Center is at least double and they don't need it. They will eventually have to pay it or migrate to Cloud.
For 2000 users of Jira Software on Server the cost in 2020 was $60,000. They would have been paying $30,000 because of the 50% renewal cost. For Data Center at that time it would have been $52,000 (with no renewal discount).
In 2023, the cost for 2000 users on Cloud Premium is $164,000 (Standard is $109,000 with less features, and with very strict automation limits). For Data Center this is $120,000.
This is the reality many businesses are facing. The jump from $30,000 to $164,000 is big jump, and Atlassian have been bumping the price of Server up to encourage businesses to migrate (25% price increase for 2023, 20% in 2022 and 15% in 2021). With those price increases the 2023 price taking them upto Feb 2024 will be approximately $51,000 renewal for 2023-2024 which is still half the price of the other offerings, so staying on Server is better for their bottom line.
We are actively planning the move to Cloud from Server. This is prompted by requirements to deploy only applications and operating systems with support. In other words, we have not choice but to migrate.
So far, we have not found any issues that would stop us from completing it. As it is, some of our users are moving to other platforms and it may come to pass that Jira's use diminish to irrelevance. For project managers, there are a lot of options available, including open source. I for one find Jira unnecessarily complicated and expensive for what it does.