Will there be any wiring problems eg series/parallel and I'm hoping to put in quick disconnects under the ash tray Also do I need to "match" the humbucker (get one that suits electrics etc)
There may be problems, but nothing that others haven't encountered before.
The rule is that single coil pickups need 250K pots for volume and tone, but humbuckers need 500K pots. If you don't do that, it should work, but your humbucker bridge pickup might not be as bright as you might want.
Seymour Duncan has a page full of wiring diagrams that should help you, even if your replacement PU is not from them.
My understanding is that you need parallel wiring to actually buck the hum, but you get higher output with serial, and my Tele has a four-way switch that allows both, and that's what I hear. If your new pickup has two wires, there's no problem, as it can only work one way. Some have four wires that would allow you to switch between one coil and two. This is often called coil tapping but that is when wire out some of your coils to decrease the output, and it can be done with single coils as well. I'm not 100% sure how they work, but I'm sure Seymour Duncan can tell you.
luser droog mentions coil splitting, which is what you actually get with the four-lead pickup. Tim suggests that a push-pull switch in the potentiometer would allow you to split the coils without changing the look of the instrument, and I'm sure there's a diagram to help.
This assumes you're adding a Tele-shaped humbucker, like Hot Rails it Bardens or DiMarzios or Lollars. If you have humbucker-shaped humbucker, you'll need to route the hole and switch the bridge.
Best of luck.