The tour pak light wiring is easy; your bike already has a tour pak wiring harness on it. If that's used for the OEM chopped tour pak spoiler LED, you will use the same three-wire connector on the bike when the tour pak is removed.
As for the rear speakers and passenger controls, give Radio Sound (HD's vendor for the OEM radio in your bike) a call and ask about what you are trying to do: (502) 267-6768. On a bike with the Harman Kardon head unit it's an easy installation. But the pre-'06 bikes used rear speakers with a CB that was integral to the head unit. I don't know if you can add rear speakers to the OEM head unit if the head unit doesn't already have CB.
You mention installing CB antenna, so perhaps you have a Radio Sound head unit with CB. If so, the bike probably already has the harness or connecting the rear speakers and passenger controls. Sorry I can't be more helpful, except to say to call Radio Sound customer service and speak to John.
Also, the speakers in the pods are 2 ohm impedance, while the Radio Sound head unit is 8 ohm impedance. You would need to change out the speakers to avoid damage to the head unit due to the lower impedance of the '09 speakers.
Sounds like a nice project; good luck.
Carl