Unlike many here, I am a big fan of Dr Grabow pipes, I just remove the filter. I think they are a good starter pipe simply because they aren't very expensive, are easily obtainable, and I find that they are reliable smokers. Although I own many "better" pipes, I enjoy smoking my Dr Grabows and will smoke at least one of them nearly every day.
Also, if you want to spend a tad more, you really can't go wrong with a Peterson system pipe as they tend to be a little more forgiving of the typical beginner packing and smoking mistakes and you're far less likely to have to deal with gurgling in your pipe.
As for tobacco, just try some different ones and see what appeals to you. Don't overlook the "drugstore" blends like Captain Black White Label, Half & Half, Prince Albert, and others. Walnut is good if you can find it. In my experience, among those types of blends there is a difference between the pouches and the tubs. I find the tubs to be better, but you may just want to try a pouch of various ones until you find what you like and then get a tub of it (them).
As for differences between types, some simplified definitions:
English Blend refers to traditional Latakia blends, but is also used as a more generic term to mean a non-aromatic blend.
Aromatic refers to blends that have added flavorings such as vanilla, cherry, rum, etc. This adds both flavor and room note that is not natural tobacco.
There are many, many others, but that is the essential difference between aromatic and non-aromatic blends.
Spending some time Googling the various terms and blend types can be very educational.
