Your suggested upgrade path is the one I would suggest and is afaict the best order.
However I would add one more step: Make a backup of your VM before you start any of the upgrades.
Please do not trust Time Machine with your VM backups as it isn't reliable for that kind of backup. Even VMware suggest you to exclude VMs from backing up via Time Machine (see VMware Knowledge Base or for more details see https://www.vimalin.com/why-is-time-machine-not-a-good-backup-for-virtual-machines/ )
The correct way to make a backup of your VM is to:
- shut down your virtual machine
- shut down VMware Fusion - not strictly required, but recommended as it makes it very certain no files are left open
- make a copy of that virtual machine to an external disk
- disconnect the external disk
Then update everything as you planned. If anything goes wrong you at least have a backup that you can fall back on.
PS: Of course you can also use my backup product ( https://www.vimalin.com ) for making the VM backup, but the steps above will work fine.
Wil| Author of Vimalin. The virtual machine Backup app for VMware Desktop Products
| Vimalin : Automated backups for VMware Fusion and VMware Workstation Professional
| More info at https://www.vimalin.com
| Twitter @wilva
| VMware Wiki at http://www.vi-toolkit.com
Wila: Thank you very much for your response. This information will be invaluable in my upgrade tasks. I will be executing the upgrades in early Oct.