SSD, Time machine & Virtual Machine

Going to install SSD in my mid-2009 iMac along with OWC temp sensor

Looking for opinions in which "order" to do the upgrade to High Sierra.

1) Install SSD, then use time machine back up to restore all files and systems including Virtual Machine, THEN upgrade to High-S?

2) Install SSD, then install High-S via bootable drive, then re-instate files etc via time machine?

Present:

Sierra 10.12.6

Parallells 13.1.1

Windows 7 Professional

Look forward to opinions....thx.