That's probably a fair point. I can't say too much as I haven't touched Windows desktop or server too much.
Could be apples vs oranges here though as we're talking about getting started versus well established setup, but my current employer is looking at adopting Ansible + Packer for imaging and partially Ansible-managing Windows servers where it makes sense because of limitations in SCCM and GPO. As far as I can see across the divide Windows Server isn't all smooth sailing.
I have a bicycle crate in my rear rack (40L from memory). I can just throw my backpack and/or shopping in there and be on my way. No issues transporting when empty. I avoid riding in the rain but I guess a waterproof bag would help for that. It's durable, the main concern is the rear rack. I had to replace the cheaper rack that I bought last year after the welding snapped in a few places over time (I had it held together with duct tape for a while). My new rack should be much more sturdy this time around.
I have access to borrow a car which I do every few weeks so I don't need to over engineer my bike setup too much.