When a person sets out to acquire a taste, the best path forward is usually one of broad comparison and contrast among subsets of that taste. This trains the brain to eliminate common denominators from perception and hone in on differences. These differences are often where you'll discover your likes and dislikes.
A person with minimal exposure to wine, for instance, tastes only "wine," no matter which wine he's drinking. But if he lines up 5 very different reds and 5 very different whites, side by side, and takes small sips from them cyclically in one setting (we're talking about very small quantities, obviously), his brain will begin glossing over the commonalities and dialing into the variations.
It's a good idea to start with a few cobs, so as to get your scorched rims and overheated bowls and chewed-up bits out of your system on something cheap.
As others have suggested, buy affordable bulk tobaccos, at first. (1 oz. samples.) No need to invest $15 per tin in a bunch of tins you never want to taste again.
Bear in mind that the baggies you'll get bulk tobaccos in will allow tobacco to dry out before long. Work through them at a good pace, and dedicate mason jars to any that you think you might want more of.
I would try one or two each of the following categories:
Straight VA
VaPer
Burley blends
DFK blends
English blends / Latakia mixtures
Oriental forward Balkan blends
Aromatics
I would have at least a bowl a day, as you cycle through these. Don't camp out in a style till you've tasted through them all. This will be creating a rough map of the tobaccoverse in your brain, and you'll pick out nuances (which you may like or dislike) which you would not pick out apart from comparison and contrast.
Have fun!