What are the hurdles of doing all new projects in cloud version and later migrating the existing projects in server to cloud?
Migration from server to cloud or vice versa is possible but in almost most cases you will loose dome data. Mostly related to apps, there is also an effort involved in migration, change in user experience, change in existing integrations. If you have clarity on your tool usage for the next few years then probably better to spend some time deciding now. Migration is not (always) a simple lift and shift process.
I hope it helps.
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