Fair enough— for whatever it's worth, I'm no fan of them either. If nothing else they really create a hard time for people reasoning about the security model of Bitcoin: There are a lot of people who have a hard time getting how the POW consensus works and then they hear about the checkpoints and say "Ah ha! this is how its secure!", after all people are familiar with centralized security so this is just a lot easier to understand.

The big damage from that comes because we're then subjected to a non-stop stream of IDEAS and IMPROVEMENTS from people who's understanding of the security model was broken by the mere existence of checkpoints, even though checkpoints do nothing relative to consensus. These people propose things which depend on a centralized security model and don't have the benefit of the checkpoints being set thousands of block in the past so they are never a practical influence on the consensus, and don't spend the mental cycles trying to fit their ideas into the real, primarily zero trust, Bitcoin security model. As a cautionary sign of where that could be going: There altcoins which user developer controlled checkpoints broadcast to checkpoint blocks in real time, and more altcoins being added that do this... as if this were an acceptable way to construct a decentralized cryptocurrency!

When headers first syncing is merged, just by adding a "must be this tall" minimum sum difficulty check we'll be able to remove checkpoints for all DOS purposes, and we'll also be able to remove them for syncing acceleration (using random sampling for ECDSA in the deeply burried chain).

Checkpoints as a cognitive security blanket against doomsday reorgs will likely stay, but we could update them less frequently, with a more regimented process, and perhaps change how nodes respond to them (e.g. a conflicting chain becoming longer making all nodes go into a safemode where they regard everything new as unconfirmed, process no transactions, and discourage any new blocks that process transactions allowing for a public resolution of the "impossible event", rather than directly coercing the consensus).