2025: install windows on new machine. Try to log in to microsoft account. Cant. Use usb key. I dont have one. Use authenticator. Message is not show in authenticator. Use password. Wrong password (it was 100% the correct one) give up and use offline account. New try to log in: nothing works. In the end i had to reset my password.
It's an easier path to go with Linux Mint or Ubuntu. Less overwhelming choices when you just want to get started. Linux Mint is good for people used to Windows as it feels familiar. If you still want to go "pure" Debian you can use LMDE (Linux Mint Debian Edition).
If Linus Torvalds of all people is complaining about how much of a pain in the ass Debian can be to install, it's going to be a pain in the ass. Hell, Mint had countless issues I had to monkey patch and would break if I looked at it funny.
You cannot expect a beginner user to touch a command line or even think about desktop environments. We're computer nerds here but sometimes the expectation that booting from an ISO or making disk partitions is easy for the average person grossly overestimates the average person's desire to debug and fight with their computer.
Seriously, ask your Grandma to install Debian on her Windows computer by herself and see what happens.
When I do, I give them a flash drive and if necessary help them change the boot order, then they just answer what they understand and accept defaults on the rest. This typically works well and they are surprised that when install is done, it's really done, no messing about with license keys and downloading install binaries and whatnot.