Upgrade from V 10 (issues and approaches)

I have an v.10 running on Ubuntu 14.04 on a physical server. I am moving it to Azure with a Bitnami image (ubuntu 20 and Erpnext 14).

I understand I have to upgrade from v.10 to 11, then 12, 13, 14. To do so, I have backed up the physical server and created a VM on my on-prem hyperv host. ERPnext runs fine on the VM.

I have tried to upgrade from V.10 to V11, got some errors. Restored from the backup and then tried upgrade the OS from Ubuntu 14.04 to 16.04. There were all kinds of error messages on either upgrade. I have spent the last two days looking through forum and google to find fixes.

Although it seems like a straight forward bench update, it is not. There is no custom code or configuration of the ERPnext. And it has a very small database. The VM size is about 8GB. What is a better approach? keep trying to upgrade on the same vm or build a 16.04 (or later) frappe bench environment, then restore backup from v.10, then try upgrading from there. At lease I will have the updated OS to build upon. The only concern is that the later Ubuntu has later python version that might not work with v.10. Any recommendation or point is welcome.

this has been asked here and answered accordingly.

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