The best option by far is to download the current installer .exe's from your Stardock Store download page to your new computer once up & running & install them fresh. You'll need to reconfigure your preferences, but a clean install is the way to go.
In fact, download all the Object Desktop installers to your new computer in a location set up for that purpose - you never know when you might want to try some of the apps you don't currently use. Be sure then to back them up somewhere else, just in case. Should you decide not to renew your subscription someday (or should the unthinkable happen to your rig) you'll still have access to the apps you paid for.
As for general preferences for the OS & other apps, there is no easy answer to that. FWIW, my experience has been that fresh app installs end up being the safest option & avoid the possibility of the new computer getting 'confused' about certain things.
Always a pain getting a new rig configured the way you like your old rig configured, especially if there is a change of OS. Just have to plow through it until all the settings options are encountered & dealt with.
Good luck!