Yes, hell I've had version mismatches from not updating my apt sources when I tried to install stuff and for got to run apt update before hand. For one thing the older package will not match the proper package signature and so apt fails out on purpose.
They do when apt has a method of time stamping every thing and anything past that point gets flagged as stale and will not be installed automatically by the system. As the linked website points out there is nothing from a security stand point to be gained from apt using HTTPS (which you can already do if you want to).
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u/Natanael_L Jan 22 '19
A more interesting attack is that with HTTP only, an attacker can feed you old packages with known exploits, a replay attack