What you can do is create a Timer based on the information in the Items. Search the forum for Alarm Clock example.
Rules do not check the UI, ever. Rules work with Items. The UI works with Items. Rules can trigger when they change or receive a command and you can send a command to Items from the UI. So for something like this you would trigger your Rule when any of those Items change state. No need to poll.
Where the polling would come in is if you want to use a Time triggered Rule instead of Timers in which case you would need to poll the Items to see if now is when it is time to do something.