Since it sounds like you're committed to making it work and will have plenty of opportunities to get the hang of it I would go with your first instinct and skip the cob (for now). The most important aspects of a pipe is that it has a comfortable bit and a good draw for you, a new briar from a popular brand is your best bet for finding that out the gate.
I agree entirely with
@Swede sage advice concerning stem material, Acrylic(plastic) stems are too hard and slick to clench comfortably and I only smoke pipes with Vulcanite(rubber) stems.
Take a grain of salt because this is only my opinion and pipe smoking is all about personal preference so I will just tell you what I think would have helped me, If I had to start smoking a pipe all over again.
I would take your pipe budget and get a few cheaper pipes, one base model offered by Peterson, Savinelli and a couple unsmoked estate(NOS) pipes off eBay, depending on the brand they are better quality for much cheaper than current production pipes look for Yello-Bole, Medico, Dr.Grabow, Kaywoodie, Willard. Look at the dimensions when buying any pipe, a good average sized straight pipe is going to be at least |5.34" Overall length| |.75" Bowl Diameter| |1.5"+ Bowl Depth|.
For tobacco I would want to get a few old-school blends that have stood the test of time and then one blend that highlights each of the 5 "types" of tobacco leaf: Virginia, Burley, Cavendish, Latakia, Orientals, in order to develop a basic understanding of what kinds of tobacco I like.
I would start with: a pouch of Sir Walter Raleigh regular, Captain Black original, Half and Half, 2oz bulk samples of Peter Stokebye PS 400 Luxury Navy Flake, PS 17 English Luxury, Lane Limited BL/WB, Cornell and Diehl Virginia Gentleman, Haunted Bookshop and a tin of Orlik Golden Slices.
You need more pipe cleaners than you think starting out, white elephant brand are my favorite because of how stiff they are and keep a couple "czech" tools around because they run away on their own.
Good luck and I hope you enjoy the hobby!