Hey Mutt,
I still consider myself a diesel novice. I've only owned my rig for a little over a year. I can't offer a lot of help, but I'll try.
RE: chips vs. programmers. Chips (Tony Wildman and DP-Tuner, sorry about the acronym there, I don't know what DP stands for either) are generally considered to be the best for performance and overall health of your rig. You can get them custom tuned to just your rig and whatever your modifications are. The beauty of chips is you can change the power right now with the push of a button or a turn of a knob. It doesn't sound like that's a big to-do, but when you hook up whatever you're towing, it's nice to not have to fiddle with plugging in a reflashing your PCM (powertrain control module). Then when you arrive at your destination, unhook the trailer, push a button and you're back to econo mode or whatever with a chip. Programmers require a reflash on the PCM.
Another nice thing about chips is that you can select MANY different tunes to choose from . I'm obviously a DP fan since I bought one. I suggest checking out their website and looking at all of the options for programs you can buy. Your Prowler weighs in at 7,500. You can get a program just for that. Oh, I also forgot a major point of the chips: They are usually considered better at keeping your egt's (exhaust gas temperature, your diesel's enemy) down. Lower EGT's = more fuel = more towing power which is the whole point of this, right? Plus, you generally get better mileage with the chips vs no chip or just a programmer. Example: I just put my chip in last week. The overhead fuel computer before the chip read about 14-15. Now in the 80 horse econo mode, it reads 19 MPG. I know the overhead displays aren't totally right, but that's a big increase, and big power, and chip program adjustability on the fly.
With any chip/programmer you absolutely MUST get guages. At the very minimum an EGT guage or you'll end up cooking the engine. Don't even mess around there.
Back to chips vs programmers. I don't know exactly how they work, but chips have stored programs in them, you just select the program you want. Programmers actually change the only program your PCM. Your programmer will contain different programs in it, and you basically load that program into your PCM. It takes a few minutes. Not a big deal, but it does require an inflight shutdown and all that.
Chips with guages also will cost a little more, but just do it. The power they make is just insane. And it's good and useable power. It may not seem like it, but I researched (and saved money) for an entire year before I made my decision to by a chip. I was going to buy an Edge Evolution (which I've heard a lot of good things and some bad about) but the guages get their info from the PCM. I don't think you can trick the PCM as easily with those. They are less expensive because the guages are built in, but the power and EGT's arent' as good.
Your sig says you have the Juice w/attitude. I think those are shift on the fly, but it still is not burned to just your rig, tire size, exhaust, and towing application. I know the Juice is a good unit, but I think the general consensus is that the chips are better. I'm sure some guys with more experience will chime in soon.
You rambled, I rambled, hope this helps...
Rob