Back in the day, David and Katie talked about the advantages of a fresh start as opposed to using what is now migration assistant. I’m wondering if folks have thoughts/advice. Is there a systematic, thoughtful way to bring a new Mac into my world?
Thanks!
As much as possible, I use Homebrew for installing command line tools and regular applications. It has a bundle which is basically a format for listing all things you installed in a single file. (Which on a fresh computer you can tell brew to install all the listed apps in a bundle file).
The other tool I use is mackup which I use to backup to iCloud all of the configurations for command line tools and GUIs (see the README for a huge list of supported apps!)
Between these 2 tools and Backblaze for the occasional file I hadn’t realized I wasn’t syncing anywhere, probably 80-90% automated. (I did a fresh install 2 weeks ago 
)
For regular documents, I sync to iCloud and an external drive my Documents folder.
I’m old school. If the Mac I’m migrating is more than a couple of years old, I prefer a clean install. I’ve found my ~/Library folder collects a lot of junk no matter how much I try to keep it clean.
Plus, I rarely choose to re-install all the apps I had on my old Mac.
Thanks. So how do you go about your fresh install? Is it simply on a need-to-use basis?
My process isn’t complex. All my passwords are in 1Password, and my files are backed up to Backblaze B2 and an external drive. So I just install my apps and copy my files.
Setting up your apps can be a PITA, but I’ve set up a new Mac or “nuke & paved” an old one more times than I can count. YMMV
Tip: I always save the latest installer for all my non Mac App Store programs. They come in handy for those “unscheduled” rebuilds. 
I’ve used Migration Assistant for years with no issues.