GM recommends you replace the clips every time they are removed, and you may want to buy one or two (or have available) of the plastic retaining covers, as they are also pretty easy to break trying to get them on.
They normally come out not too bad, but to get them in all the way, you need to make sure the line is pointed straight in, as there is very little clearance in the hole it goes into, so it jams up easily if you go in at an angle. The ones into the transmission can be more annoying to do, as with the exhaust and various brackets installed, there isn't a lot of room for your arms to get in there and also be able to see what is going on. And if you are doing this on the ground (as in, not using a lift), I would suggest just lifting the truck enough to get under it and so you can move around, so you don't have to extend your arms as much to reach to the ports on the transmission.