Checkpoint is a weird card, and I'm glad it exists - because Code Gates, IMHO, should require you to twist your brain to use/defeat them effectively.
Clearly 4 for a strength 7 code gate is great value, and on the face of it, trace 5 seems pretty strong - and how often can a runner sustain 3 meat damage? I've Had Worse and Plascrete Carapace not withstanding.
The thing is - I would say that Weyland does not trace well. SEA Source works fine in Weyland because it's a one-off trace that usually leads to a flatline, and if there's one thing that Weyland does do well it's having a boat load of disposable - but Checkpoint is not usually a one-off end-game trace, it's a subroutine trace that may well fire repeatedly. Spend too much money tracing, and the runner can simply jackout and run again - slowly draining the corporation coffers.
The other thing that Weyland does well, of course is Bad Publicity - giving the runner free credits to spend to help evade the trace. Suddenly the trace 5 looks more like a trace 4, and if you're also playing with Hostile Takeover (and why wouldn't you?) - well, it doesn't take a huge amount of to render Checkpoint pretty tame.
So what is Checkpoint good for?
In Weyland, you might find a way to use it in front of a remote as part of a kill combo. Stick it in front of a fully advanced Posted Bounty or Vulcan Coverup and maybe you can jack the trace up so high as to force the runner into a situation where they are damned if they steal the agenda and damned if they don't.
Checkpoint could make for an interesting splash in protecting Jinteki: Replicating Perfection remotes - synergising with Excalibur and Enhanced Login Protocol. When each is a precious commodity, jacking out to re-run doesn't always seem like such a good option.
For protecting centrals, splashing Checkpoint into NBN: Making News with ChiLo City Grid works really well - but if you're playing NBN you already have access to Gutenberg so Checkpoint is probably overkill (and if you're that determined to tag the runner you probably want to save the influence for Scorched Earth and Traffic Accident).
(I cannot think of a single example in HB when you would want to splash this card - but I would love to hear some.)
@MrWeasely has already mentioned the synergy with The Cleaners - if you are playing wide (Gagarin Deep Space: Expanding the Horizon kill deck new meta?) then Dedicated Response Team is probably also a good idea. Maybe in the server protected by Checkpoint (trollolololol)