It's just whether it is worth me buying a second hand 13" 2018 model now with Applecare vs waiting and seeing if anything new appears at WWDC.
I'm definitely in the waiting boat. I wanted to upgrade when I started playing with VMs. But I set up servers (ProxMox) both at work as well as in the office that are more capable of doing that. So my late 2013 13” is still okay for all the other work I do on it.
TM is definitely better then any of the solutions I've seen in windows. I'm mostly on OneDrive at this point and so much of my data is in the cloud and so a backup solution like TM is less of an issue.
I used to file-copy my data as well. Worked really well for, don't know, 15 or 20 years or so. But with a NAS full of stuff and a couple more PCs in the house, it's all a bit of a hassle. Happy I can just let the Mac do its thing and not bother. But yeah, file backups are also a good discipline. I remember not caring if I had to reinstall everything. I had the files and the computer was clean again.