Since you can run both machines at the same time, I think it is worth doing a manual transfer. Frustrating and slow but worthwhile.
It will give you the opportunity to figure out which apps require deauthorization, which require explicit saving of preferences/data, etc… The information will be very useful in case you have to do a nuke and pave. Also it will let you evaluate which apps no longer have a place in your workflow.
Or, as I learned the hard way, some apps will install a limited number of times then lock permanently. Now I always deauthorize (remove licenses) before reinstalling an application.
I’m going to be in a similar situation to @SteveU75, and that’s what I’m going to do, for all the reasons you mention, and to avoid any cruft from getting transferred into my new system.
I use Homebrew regularly but never this bundle idea. However not everything I want to use is Homebrew-ed; for example GNU’s gurgle report writer — even if somewhat out of date — would be useful for some projects I am involved in but it isn’t on Homebrew neither is PSPP (GNU’s re-implementation of the stats package SPSS).
I like to do fresh installs because after a certain number of years I accumulate a bunch of software I no longer use. The software has to earn a place on my new laptop. It is more effort, but worth it to me. Since it has been over 11 years for you, I bet you have a large list of unused apps installed.