Your story sounds just like mine, lol. I've been using my trusty little Wacom Bamboo (yeah the "cheap" one) now for about 3 or 4 years. The installation software had some basic use tutorials that I followed and i watched some tuts on youtube aswell. It took me a month or two to get used to looking forward at a screen while having my hand do the drawing on the desk.

My advice for getting the closest results to hand drawn graphics on the digital medium is to play with your sensitivity settings in the tablet software itself. There is a sweet spot with those settings and your brush settings in whatever drawing software you use. Took me the longest time to first figure out that there was a sweet spot and then find it. It felt really funny for me when i started out but as i stuck with it, it felt more and more natural. In photoshop there is a check box called "Other Dynamics" if you check that and set the options in it to "Pen Pressure" then you wont have to play with the opacity and fill of the brush you're using to make your strokes lighter or darker. It will automatically be based on how hard you press just like a pencil.

I'm a big subscriber to the idea that one of the best ways to learn something is dive right in and play around with it. With a tablet, I think it applies perfectly. Good luck