I recently ran new wires to my doors
I actually had the interior except for the dash and headliner out. Makes it easy to work when the seats are out of your way.
anyway, you are gonna want to use some wire coat hangers to get you thru the door jam grommets. Basically snake them in there best you can. I put some in from the door side and some in from the body side. you just have to feel it out. I also pulled the ECU out of the way. Didn't un-hook the electrical but got it out of the mounting strap so i could work behind it.
The rears will be easier if you unhook the factory wire harness just inside the B-pillar and then free the grommet containing the whole bundle from the body. once you have the hangers run thru, just tape the speaker wire to it and pull it thru. Its not really that hard of a project. It took me about an hour to actually run the wires once i had the trim out of the way.
As for the wire, i think it really depends what your other equipment is. I have a pretty nice HU and just pioneer 3-ways in my doors. Good stuff but not top of the line stuff by any means. I used some regualr 14g speaker wire. I think it was a good choice. I had a 50ft roll that left me with enough to be comfortable. you can get a 50ft roll of automotive speaker wire at walmart for <$10. They had 18, 16, and 14g but not all the stores really keep a good stock of it so you might have to check a few stores. its not high end wire but again thats were you need to be realistic if your other compnents require high end (aka $$$) wire or not.
Once i had all my wires thru the door jams i ran them along the rockers to under the dash. I came across the front floor and then ran them up to the HU in the center of the dash. You will want to again fish something thru there to help you pull the wires up. You can also take your ashtray out as it gives you a little more visibility when you are working the wires up.
Now i had the seats, console and carpet out when i did this, so i'm not really sure how difficult this last step will be if you are just pulling the carpet back to run the wries over to the center of the dash.
As for your 2nd set in the rear. are you planning to put them in that lower hole in the door? Few things i have thought about with dong that...
1) there is no grille there so unless you are cutting up your door panels it may not really help the sound at all and may actually hurt it.
2) you may want to check with somebody more knowledgable about what running 4 speakers off that rear channel is going to do with the ohm load. Don't really know if your HU is as flexible with loads as some amps out there. but i know it can come into play with subs so i don't see why it wouldn't with door speakers
3) lots of people often say that the rear is for "fill" and not to over dominate the sounds up front. I don't know if you are chasing a loud system with 4 speakers out back and 2 up front, but it may "shift" the sound in your truck to the back.