Installing an amp is much easier than you think, only a couple of connections. As I mentioned before its just the routing of all the wires that takes the bulf of the work. If you feel comfortable taking apart the interior much of the hard work is done, its just time consuming. Honestly, the speakers will prob be tougher to install than the amp. If your unsure about doing it yourself, I would leave it up to the pro's. I would check out a few local car audio shops and ask about install prices. Most shops here in AZ, will offer a deep discount/free install as long as you buy from them. Just have to pay for wiring kits and any parts they need to install. Also ask if they will install stereo equipment not bought from them. Sometimes you can buy the stereo equipment online cheaper than the store prices and that will offset the higher install price they charge for not buying equipment thru them. Also, might wanna check out Craigslist for installers. Might be able to find an installer that will come to your house and put everything in. Just some things to think about since you do have a budget.
Now here's the tough part, Sound. What might sound good to me may not sound right to the next person. If you go to a stereo shop, ask to demo the speakers they have. this can help narrow down what you like. I've tried multiple different brands of speakers and I always end up going back to Boston Acoustics. They just sound the best to me. For your front speakers I would go with a 6 1/2" component set. For the rear doors you can get away with an average set of coaxial set of speakers. Just about all the sound you hear will be coming from the front speakers so I would invest more money in those Vs. the rears.The truck comes with 6x9's in the stock front doors. You will loose some bass by going to the smaller 6 1/2" speaker, but the sound quality of the 6 1/2" will be worth the trade off. You can install a sub later on down the road if you want more bass.
As for an amp, you don't have to buy a pioneer to match the headunit. Amps can hook up to any headunit, doesn't matter who the manufacturer is. Some of your better brand names are Soundstream, JL, Boston Acoustics, Rockford Fosgate and so on. Now there are endless setup options to choose from. I would wait till you have some speakers in mind before looking at amps. The speakers will dictate the wattage of the amp. Only look at RMS. You don't have to match it perfectly. Lets say you speakers are 100W RMS, you have 2 amps to decide from. Amp 1 is 75W RMS and amp2 is 150W RMS. Go with the higher wattage amp. Under powering the speakers is bad and you will be running the lower wattage amp to its max. Its better to be able to turn down the higher wattage amp than max out the lower one, plus the extra power will make the speakers sound better. Also, it will provide some flexibility later on down if you want to change your setup for some reason. As for how many channels, again you have multiple different options. You need at least a 2 channel...obviously, to power the front components. I don't know the rating of that headunit, but it more than likely not be enough to power the front components. Again, your best sound comes from whats in front of you so focus more on the front speakers. You can buy a 4 channel and only power the front 2 speakers and leave the other 2 channels open and power a sub off those later if you decide you need more bass. A 4 channel is bigger than a 2 channel so mounting options will be limited. These are just a few of the endless setup options you have. I can keep going, but my fingertips are bleeding!! haha Any questions about anything feel free to ask, I won't be a jerk and try to help where I can. The planning stage is tough, but take your time, many many options and in the end it will pay off.