I think you should do whatever works for you. I like my Flake dry enough to break or almost break when I fold it. Take a flake, fold it in half along the length. Then fold it the other way. Grab both ends, give it a very slight twist to loosen it up a bit. Gently push with slight twist into bowl until it bottoms out, push a bit more to expand it out but not too hard. If there's room left at the top, sprinkle some loose pieces to make lighting easy.
With some experience, you'll get a feel for how big the Flake needs to be to fit a specific bowl. Tear off a bit length wise for smaller bowls. If I chose too big, I pull some off/out when I stuff it in the bowl. Better too loose than too tight, you can fix it with tamping. What I pull off becomes ready rub for the last bowl or two from that tin.
All of what I described is done in ten seconds or less. The most important things are for the Flake to not be too moist and error on packing loose vs tight. You can fix too loose with some good tamping. The fix for too tight is the skinny pipe tool to loosen up the tobacco, empty the bowl and start over. I use this technique to pack and smoke three to five bowls of Flake per day, it has worked well for quite some time. Check the draw before you light. Occasionally, a piece of tobacco may obstruct the draught hole at the bottom of the bowl. Running a pipe cleaner all the way in and twisting usually clears the obstruction.
If your personal preference is to use Flake that is more moist, stuff looser to allow for expansion when the tobacco heats up. In my opinion, you'll enjoy more flavor, less hassle and avoid tongue bite from steam if you let it dry out more but to each their own.
