I tried drawing in illustrator once but just couldn’t do it.
I haven’t tried the bamboo myself, so I can’t speak for how pressure sensitive it is, but it’s a good start to practice the hand-eye co-ordination you need to be able to draw one one surface whilst looking at another, it took me about a year to get used to it fully! But a lot of my friends picked it up a lot faster.
If you can imagine, pressure sensitivity is more like using a brush, so you can go thick to thin to thick again in one stroke. A good example of an artist that uses brushes a lot is Paul Pope. Without pressure sensitivity it’s more like using a fine-liner pen which has a fixed line width, which a lot of artists are used to anyway. An example of an artist that predominantly uses fixed width is Geoff Darrow.
If you’re working in photoshop, depending on your version, try pressing ‘R’ to rotate the image whilst you are working, this way you can draw and follow the natural arc of the human wrist (going from the bottom left to the top right etc.) and it feels more natural, as you would rotate a paper of paper when you’re inking.
Another tip for changing brush tip sizes whilst drawing is pressing the ‘[’ and ‘]’ keys.