Having reinsulated my own attic last spring, I will give you my experience.
It is not that "tricky", except that you need to be careful in the attic to not step through the ceiling, not bang your head on the rafters (or rusty nails), and not get heat stroke. To avoid these problems, you just need a few chunks of plywood to move around the attic to stand on, some patience, and take a lot of breaks.
The only things you really need for the operation are:
- The aforementioned plywood
- Dust Masks to protect from inhaling fiberglass
- Goggles to protect your eyes from fiberglass
- A box cutter for each person involved
- Long sleeved shirt and jeans to wear
It's not that difficult. You bring the rolls up into the attic and roll them out in a straight line. If there are obstructions, or your roll is longer than the length of the attic, you cut it. There are other safety considerations for insulating around ducts and electrical, but you can read up on that all over the internet.
It took me 2 days to do the attic of my townhouse. The first day I had my buddy there to help. The 2nd day, I pulled a 12hr day up in the hot attic to be done with the whole thing.
Good luck!