This is all great text, and the bolded point is one that is very, very easily overlooked. An equally-spec'd machine will be around the same cost. It's so easy to get lost in spec sheets, feature comparisons, etc. It takes some care to ensure you're actually comparing fairly.
A $300 all in one is usually using a 3-4-5 generation old CPU with basic chipset and plenty of corners being cut. They may also be using chips that failed for top-end rollout. For instance, a lot of early Core i3 chips are actually i5 chips that failed speed tests or that have 2 dead cores. i3 chips can be fine for reading email, but begin to bog down pretty quickly on a lot of task switching or background tasks.
Hardware-wise, a similary spec'd WinTel will be the same price as a Intel Mac. The Mac seems to have a longer life cycle than Windows machines and that may be a function of Apple choosing to caste off old code when it hinders optimization. The claimed strength of Windows (backward compatibility) is also it's greatest weakness (tons of legacy code to slow it down). Of late, even M$ has taken to cutting loose some old code for the same reasons.
I find that the Mac ends up costing less as a whole because it includes a lot of utilities and functions in the OS that are "extra cost" 3rd party tools in Windows. Also there seems to be a lot of free (or pay if it's useful) tools for the missing pieces in the Mac. For "heavy hitting" programs, that can be a wash since most of those companies make versions for both.
If you get into the Apple ecosystem, there are some really powerful functions in the macOS. You can share screens (phone, tv, computer, tablet, etc.), use the phone/tablet as a touchpad, hand-off documents so you can work where you left off on any other machine you have. If you have one Mac on your network and fire up a new one, the OS will see it out on your network, ask if you want this machine set up like the other (letting you choose, app+data, data, apps, etc.), and once you answer a security question, it asks your user name, password, and then asks you to go away while it clones your new system. All pretty hands-free and never failed for me.
Talk about an enterprise game-changer and it made it clear why our IT department chose Windows (to justify it's existence).
Yes, it's easy to get a well-enough-performing Windows machine for less initial out of pocket than a Mac. Impossible to argue that. But IMO the savings stop there.
For 15 years, among other duties, I was a Windows admin, and I won't willingly go back to that life. Windows 10 - and the Windows 10-X rebuild is supposed to be so much better, but at this point, I couldn't care less - for home, I'm a Mac guy, and so far, for work, I'm still a Mac guy.
That's not religious zeal; I just can't and won't go back to giving up so much time to keep Windows machines clean and running optimally, especially when that's the result of having to install stuff that should just be built in, or has to put a big shield around the OS.
There's a reason why Windows is toying with installing a *nix kernel, and supposedly will be fully moved over to a *nix kernel after the 10X rollout is complete.

We'll see. Microsoft is moving away from desktop as a primary focus and is putting a LOT of eggs in the Azure basket. Going with a Linux based solution this late in the game feels abandoney and giving-uppey to me.

<- redux
I have a new Macbook Pro 16" for work, my 2013 15" MacBook Pro - which was used and working fine when I got it - was rolled over to Liz's desk as her new desktop replacement, and her 2011 iMac has gone to the kids for online schooling, and "it all just works". I just updated the iMac to Catalina, and all it required was a file system update in place. Let that run overnight and whammo, all done, no hitches, no roll backs, nothing. 2011. Not bad.
Meanwhile, I hear a lot of four letter words and frustrated tone when she has to use her brand new work-supplied Windows 10 32 gig, i7, SSD driven notebook for mostly-Office-based tasks.
Again, this isn't zeal; it's experience.