I've got a 2019 Dunhill tanshell poker with silver army mount that smokes as good as anything else in my collection. Anyone even bothering trying to trash it as a crappy smoking pipe simply has no idea. They make fine pipes today. They made fine pipes in the last decade, the one before that, and before that, and before...
Obviously, if you're just thinking about getting the job done, spending a grand on a pipe is pretty fucking stupid, isn't it? But perhaps you just enjoy a certain style, shape, colour, provenance, history, weight, stem material, or combination of that you just can't get for $50.
Who cares?
You can't take money with you, so as long as you're not going into debt or neglecting other essential things, worrying about the money spent on a pipe is wasted time. You'll likely waste more money on much more useless things than a pipe.
I like the couple of Dunhill pipes I have, but what I enjoy most are my Tom Eltangs. Now that is a 50th year marker treat.
A lot of his work comes in at a higher price point than you initially indicate (not all does), but I doubt it's out of reach. To me, it has been worth every penny. His work is some of the best in the world, but that's just my opinion.
You can find a lot of classic shapes in his lineup, albeit with Danish styling, which I am a huge fan of, so I'm biased. I like classic shapes with Danish minimalism. I find it very beautiful, functional, and pleasing in the hand. Maybe it appeals to you. They are all excellent smokers. Tom Eltang makes a point of that.
If you get twisted up in knots over the price of your pipe, consider if you're really going to miss an extra couple or few hundred bucks in 5 years. You probably won't. So, spend it on something splashy for your 50th birthday. Maybe you have some years ahead of you yet, but the brutal fact is that you're soon destined for dust. It's just how it is. So enjoy it while you can.