Oh Boy. I'm not sure how to answer this. I have been smoking a pipe for 30 years and my tastes in tobacco and pipe have changed considerably since thenn. I think it is very personal to the smoker and the only way I found what I prefer was by trial and error. For me, it is based on room note and flavor. My Uncles and great grandfather were pipe smokers and smoked various inexpensive black Cavendish blends so I have a tendency to be drawn to them from either familiarity or nostalgia, or both. I was lucky to have a close friend who worked for years at the local tobacconist that introduced me to a myriad of flavours.so many options and so many listed here. As for your personal preferences; what personally do you look for in a tobacco? why do particular blends appeal to you? How do you choose your Tobacco and what makes it good?
It's like asking what your favorite adult beverage and why.
In my youth it was PBR and vodka, because they got me there quickly, then the micro brew faze of the 90s, now at my age I have whatever floats my boat at the time. PBR one night, 30 year old single malt another night.
With pipe tobacco, some days it's Captain Black in a cheap corncob file mowing the back forty on the tractor, next day it's Lane Ltd in a high end Peterson on the front porch.
The bottom line is, for me, I am always trying new blends and then smoking what suits my mind at the time. It is a very individual personal choice and no choice is wrong. Find what YOU like , not what someone tells you that you should like. You will know it when you find it. And then at some point your tastes will most likely change, as comes with age, so it will stay interesting.