1) Is it really that simple?
Yes, just boot your physical server from new vSphere 5.5 installation media and the installer will detect a old version intalled and ask you for upgrade or overwrite.
2) No chance of losing my VMs?
Backup is always recommended 🙂
3) Do I need to shut down those VMs first?
Yes, since you will need boot your physical server from vSphere 5.5 installation media,
Can I use my new clean ESXi 5.5 host with the VCenter appliance and new web client to connect to the older 4.0 host and copy the VMs from the 4.0 box to the 5.5 box?
This VMs are stored on local datastore or shared datastore ? If on datastore you can map the same LUN to both hosts and since you don't have vMotion license, just shutdown the VMs on 4.0 host and restart on 5.5 host.
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Richardson Porto
Senior Infrastructure Specialist
LinkedIn: http://linkedin.com/in/richardsonporto