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In terms of saving money consider that your current machine has lasted 10 years. If you plan to use the next machine for approximately that length of time (which would be awesome) spending two or three hundred extra dollars now will pay far into the future. If you buy from Apple apply for the Apple Card and save 3%.
 
OP wrote:
"Sounds like the odds of finding a 2019 27” with a SSD would be super random."

As colodane wrote in reply 25 above... "educate yourself".
No one else can do this for you -- it's up to you.

The best way to get a 2017 or 2019 iMac, configured the way you like, is from the Apple online refurbished store, which is here:

But you must "learn the rules" about shopping at the online refurbished store:
- items come in, and go out, often quickly.
- you must check (literally) morning, noon, suppertime and night to see what's available.
- you must check CAREFULLY the configurations of items, to be sure you're getting what you want.
- you must be READY TO BUY when you see something you want -- it may be gone in hours or even minutes.

Apple refurbished Macs come with the same 1-year warranty as new.
You can also buy AppleCare for them, if you wish.
 
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