I’m in the same spot, we are debating what makes more sense right now. I’d love to hear opinions. 

I have done our documentation for a new deployment which was fairly straightforward once I understood the NATs portion.  

Is it weird I’m excited about proxy pools? :)

Nope cause we are too to help with processing and load.  They are great too being able to assign storage to the Pool now versus Proxy alone.  

Why migrate to a new environment?  What benefit does that provide?  If you bring in M365 backup storage to a new server don’t you lose all restore point details (data is there but not by restore point).  I’m not sure any option other than upgrade is correct.

Thanks Tim.  This came from a colleague so we will be discussing it before we proceed anyway.

What would you say the LOE is to spin proxy pools after upgrading? Easy?

Yes very easy to get Proxy Pools going. 

Great to hear. 

I’m very small obviously with 9 tenants and 883 licenses, so I don’t have a need for Proxy Pools...at least not yet.  I do plan on migrating more over to VB365.  With that said, I just ran an upgrade, and nearly on a whim.  And from our local aquarium even.  It really wasn’t bad.  I didn’t see a reason to rebuild, for sure at our scale.  The main thing for me was that after the update there are post-upgrade steps to take such as updating the repositories and updating permissions on the registered application, so that did take a little bit, but since it was only 9 tenants, it really wasn’t that bad at all.  Then again, I would have needed to take those steps regardless of if I built new and migrated or performed an upgrade.  Like most things VB365, it all went pretty swiftly.