Welcome to the forum and Community Simon.
I am 26 and have only been smoking for about 2 years. I was similarly overwhelmed by the prospect of thousands of blends and pipes staring me in the face. I watched a million YouTube videos and read this forum like a fiend. Packing techniques, tobacco reviews, pipe maker reviews: I lived and breathed it that first year. Then I went home to visit some family over a Thanksgiving holiday. My dad, also a pipe smoker, was sitting with me out on the porch. He with his ancient stanwell, and me with a Nording. He stared at me dumbfounded as I fumbled around with my pipe restuffing it several times, messing with pipe cleaners, never setting my pipe tool down, and fidgeting with the lighter. He looked me dead in the face and said, "Boy, you're thinking about it too much. Just smoke the damn thing." So I did.
Starting out in pipe smoking is much more enjoyable if you just go with the flow. Everything can get picked up just by experience. Ask for suggestions to problems or when looking for new blends sure, but make sure that relaxing hobby of yours is actually a relaxing experience. This second year I just do it. Take my monthly self-appointed allowance, and branch out to find stuff I like or haven't tried. Patience and persistence will make smoking a pipe an experience you won't want to live without.
I'll also add that beginning smokers get in their heads what they think they will like and not like. I think eventually, again through experience, we find out what works for us. I was really put off by using a cob pipe when I started, but I found over time that nothing was better for me to use in the car when I needed to clench. Go with a simple aesthetic you think you might like, and then think about what you like and don't like about the function.
I recommend a lower end savinelli, peterson, or stanwell to start if you want to go briar. Plan on spending 60-80 dollars American on a new low end, or look for estate pipes on eBay or etsy for awesome deals. Avoid a poorly made basket briar when you start. I would hate for a poor pipe to put you off. Cobs are also a great way to sample tobacco as well.