“A majority of the Chromebooks with come with an 11” screen"
So, does this mean mine would come with a smaller screen or larger screen?
Could, not would.
I’m guessing that, at this price, they have all reached their end of support dates and are no longer being updated … ?
Correct for the majority.
“Majority will be EOL” and not receive OS updates.
EOL is end of life 
How many weeks would this be a useful piece of technology to own?
I got a HP Chromebook 11 G4. For the $50 on Amazon I could have gotten a HP 11A G8 a MUCH better model only 3 years old instead of this 8 yr old Chromebook. I think the price point needs work on these mystery deals. It should have been $40 so I at least feel like I got SOME SORT OF DEAL. This feels like a losing scratcher ticket.
Return it?
If you’re unhappy with it, reach out to Woot! Customer Service. To speed things up, let them know if you prefer a return/refund or a replacement (if possible).
Please allow 24-48h for them to respond.
Browser: Use the Woot! Customer Service form.
Woot! App: Choose Account from the bottom navigation and then Support.
Note: Woot! Customer Service replies go to the email address on your Woot! account, not your Amazon login email if used/different.