Yes they will go again if you did a psp. Once it turns into a policy the machines should try again after the 24-hour wait period, or you can go into the task and retry the selected failed machines. We have a open ER that they are addressing regarding this very problem, and they are looking into a policy/task queueing system to fix this.
We use the beta support tools that builds in a ton of right click functionality when you select a device. You can even add to it by editing a XML file. One of the options is a policy.sync. But there is a script in managed scripts that I have created a static task for so I can drop multiple machines into it and policy.sync more then one.
It's called Package Sync. I made a copy of that and removed all lines of code except:
; Start the policy sync program; no need to wait for its completion
REMEXEC2=c:\ldrunner.exe <qt/>%LDMS_CLIENT_DIR%\policy.sync.exe<qt/>, /ASYNC
Beta Support Tools: