It's not hard, it can be a bit messy if your not careful. Very straighforward though, remove bolts from the pan, drop it (this is the messy part, because most auto pans don't have drain plugs in them, so getting the pan off without spilling a few quarts of fluid can be tricky), pop the filter out, put a new filter in, bolt the pan back, fill fluid.
Some say you should then disconnect a line going to the fluid cooling, put it in a bucket, run the engine for a small spell until clean fluid starts coming into the bucket, while pouring more fluid in the fill tube. This replaces all the fluid in your torque converter as well. Shops have a tool for to make this job easier. Some say it's not nessesary, some say it's entierly nessesary. It's up to you. ABout 30-40% of your tranny fluid is in the torque converter.
Beware, if you take it to a shop and ask them if you need a rebuild, statistically speaking, the chance of them saying you do is alot higher. Tranny shops are notorious for showing you a pan with lots of stuff stuck to the magnet (very normal BTW), and telling you that you need a rebuild.
You should be able to tell if the trans is in dire need of a rebuilt by how it drives. Does it slip? Does it surge? Does it shift the way it should? If it's not acting up, I wouldn't rebuilt it just for fun, unless your tearing the truck down anyway.