Alright, I figured out what's going on here. Sometime ago I transferred all my coins from my bitcoin core to Coinbase. This transfer was conflicted as well until it updated. So the reason why the payment I sent never made it is because I didn't actually have any coins in my wallet, though it was showing so since I was so far behind on transactions.
Ditching Bitcoin core forever, it's way too slow and really hogs resources on my PC. Sorry for the confusion!
Huh. Strange. Try starting it with the -rescan option this time. You don't need to have -zapwallettxes anymore.