Most everything is in the title.
I’ve got to take my old desktop down and start fresh as the old one has out lived support. It is lacking a few things to be able to update to windows 11 and things have come a long way in the last 7 years anyway.
Things I’m already thinking of, tell me what I’m missing.
I would have thought Windows back up would be similar to Mac. You just take a regular backup, then select what you want brought in to the new machine.
My laptop is 12 years old but my ex got a new Mac a couple of years ago, and it was a simple as taking her backup drive (which is permanently connected and constantly update), plugging into the new machine, and selecting everything like documents, apps, and such. The apps that were not compatible were simply displayed when copied over, or would show they needed to be updated when first opened.
A thing I often do is preserve the hard drive (or SSD) from the machine for upgrades and reinstalls. Drives are inexpensive these days. Take the old drive out, put in a new drive for the new install on the old machine if needed. You can get connectors or docks to read from the old drive via USB, or just install the old drive in another open drive bay of the new machine, if you have one available. Then you aren’t risking deleting anything you might need.
Alternatively, use something like Macrium Reflect to make a full disk image to an external drive before you wipe it.
This is why I’d be a Mac person if not for 3-4 programs that I “can’t live without” that are windows only.
Yes, good thinking. I’ll definitely not wipe the old C drive SSD until I’ve been up and running on the new for at least a month.
If you don’t use a browser that backs up your bookmarks, your bookmarks.
Windows backup tracks everything but data, so it’s definitely useful if you’ve got fiddly settings. I like starting completely fresh as I may not want things the same way they were before 
If you don’t use a password manager that stored off your c drive, all your passwords. Especially if you use the internal Windows one, be sure that’s backed up somewhere easily accessible.
So data to a spare drive, or the cloud is the big one, but you have that covered 
Check! All my browsers keep my bookmarks
This exactly, every 7-8 years I get to get rid of all those pesky drivers and such from past experiments so all the programs will be clean installed.
Yup, everything I want to keep is going to Dropbox so it will be available to me everywhere. I think this will be literally days as I didn’t realize what all had accumulated on the C drive and nowhere else. I’ve thankful I was forced to move on before it died.
Backup your browser profile. When I restored my profile it has all my tabs were I left them.
That is the ONLY thing I don’t like about my Mac. LOL I had an old driver or setting or something that kept popping up related to an old wacom tablet from a long time ago and it took a lot of work to get rid of it. lol
–
Make sure you have any passwords that aren’t going to carry over.
First log in on Colossus, wish me luck. Lots of installing to do over the next several weeks.
Ha, I named one of home servers Colossus, it has an attached SSD named Guardian. The admin is Forbin.