Visvanath Ratnaweera

Reason for me not being able to give an useful answer, apart from being a non-expert, is that we are invited to compare many things:
- Windows vs Linux
- In-house vs hosted

- different virtualization platforms (ESX, Hyper-V,.. vs. AWS, Azure)

- Conventional (native) vs containerized

I'm sure, there are experts from each field in this forum, but rarely an expert in all of them!

What we shouldn't forget the HR factor. Luis is one of our (rare) Windows experts. Are his bosses trying to teach an old dog new tricks?

I need to be careful, what I'm talking about. "Cloud" is something I don't have the slightest clue. Better leave that out. If you compare on-prem VMs with VMs at AWS (or Azure or wherever) that is straightforward. Note that the BIG offer a multitude of products and as many different jargons. But they also have conventional VMs. Think of this as as comparison of own VMs vs foreign VMs (VPSs). The differences are easy to figure out.

If those VMs are not conventional but Docker platforms, that is a complete different story. I have not enough first-hand experience to say anything. There are more suitable persons in this forum, and the top professionals in the "Large-scale Moodle" break-away group some years back.

assignfeedback_editpdf is an annoyance. See MDL-71909.

A common scenario is Moodle doesn't recognize the existing database and creates new one. For example, the database hasn't been restored or for some reason the database prefix (usually mdl_) changed. In your case unlikely since you have upgraded Moodle earlier and recognize when you are taken to the fresh installation routine. Also you mentioned empty courses, which freshly installed Moodle doesn't have. One never knows.