Chris...
While I am no guru on antenna's I will try and offer you a well worded opinion and your options.
First antenna choice is important as is the placement of the antenna on the vehicle for maximum efficency & performance. You need to decide on your own if drilling a hole in your roof is really what you desire for antenna use or is the magnetic base ok for your desires. While there are alot of magnetic antenna bashers out there they still do the job asked and can,depending on what you buy,utilize the power from most export radios or amps. There are negative sides to them of course,scratching of paint when applying or removing them,possibly blowing over in high winds,etc etc. IF a ready-to-use magnetic style is what you want,then I'd reccomend the Wilson 5000 for a few reasons. It has the capabilities to handle extra power loads,has a large enough magnet that once in place its not going anywhere and can be tuned easily.
Now if your deciding to go the roof(mirror mount shaft antenna usage mounted style)and planning on drilling a hole I would use a polyurathane beehive mount(they can be had in most any color) and a good coax(preferably Mini-8u or better). The antenna decision can be wide and made by you to suit your tatse then. Most any of the higher end stud mount antennas will then fit your bill,just stay away from store bought,shelf riding truck stop BarJan crap. The Wilson you said about above will work,however consider the 18" shaft and short stinger when your truck runs down the road. With that much shaft they shake bad at speed and will come loose very easily. IF you desire that Wilson 2000/5000 then use a 6" shaft with the longer stinger top,Much easier to maintain and keep tuned.
I'd stay away from fender mounts on our trucks. If you'd ever see someone who has had one for a long period of time and see what it does to the hole you use and the tweaking it does on the fender in the wind then you would understand. Mirror mounts on the Chrome early second generations are also not a good mount. They are not grounded suffeciently to allow for proper tuning and while they may tune at first for you,a trip down the road with a wind load on the antenna would be enough to break the little ground you have and ruin a radio. Twin antennas on the bed sides or just inside the beds are popular but will not function well. They true co-phased antenna system needs to be 8''6" apart to tune properly and work correctly. I have seen one mounted in the center of the bed behind the cab and as long as the height of the antenna goes above the roof and its mount grounded well its a good placement spot. Bumper mounted 102" stainless whips work very well and can handle any amount of wattage you need to use.
In my work truck I run either a Connex 4600 Turbo or a Northpointe NT3HPbacked by a Dave Made M80(takes a 5watt input and then deadkeys 80watts out with a 250watt swing). I use a antenna built by one of my fellow drivers here at work which we mount and tune by both swr's and ohms(ohms being the more efficent method). I have no problem chatting with my fellow drivers and either setup can handle the distances I need to chat.
I don't run any CB in my pickup at all,LOL. After spending near 3000 miles a week listening to all the squawk all week long all I want to listen to is my Cummins and the stereo ripping those wonderful sounds. I hope I helped and if you got anymore questions feel free to drop me a PM here or at Cummins Forum and I'll try and answer them for you... ..... Andy
P. S. -Before you buy a antenna if a stud mount is what you desire,drop me a note as I will go look into my musty old closet and see what I have lieing around I can send off to a new home. After running the "old mans'' antennas I don't think anything else will ever be used.
Attention: TDR Forum Junkies 
