Eastbank,
Back in film days I eventually settled on Leica rangefinders in 35mm, Mamiya rangefinders in 6x7, and Hasselblad and Rolleiflex in 6x6. None were cheap, and the cameras did require maintenance on occasion, and yes I paid for that. But a 40 year old Leica M lens with brass showing and a few dents from hard use was still a solid, reliable tool that rendered scenes in a very pleasing way. I used a number of beat-up lenses for personal projects and to make money for years.
Current cameras are different, but I'd make the same recommendation about lenses being worth a higher investment than cameras as I would with scopes deserving more of your budget than rifles. That's just my take on it. (And to answer your implied question I settled on current Fuji camera systems, and tend to buy prime lenses for the marginal improvement in image quality over the zooms that are more convenient and often cheaper.)
Please don't consider this a personal attack, or an attack on Leupold. I've got a Leupold scout scope on a rifle that's served well for a couple of decades. There is nothing particularly wrong with their scope range now, either. But when you bring Elcan, US Optics, Swarovski, and others into the equation my priorities and wants shift a bit. I'd prefer to spend more on a marginally better product, and that was my point.
If Leupold fits that price/performance point that works well for you then please enjoy them. They are solid products from a solid company, and you can enjoy them for your lifetime. For my personal rifles the precision guns have US Optics on them (purchased well-used, but US Optics will disassemble, clean, and rebuild an old scope for a bargain of a price), and the carbines have EOTech sights (less for image quality or design -- this is mostly about the fact that with my eyes an EOTech offers faster target acquisition than the alternatives I've owned.) If I had a higher budget I'd probably move to
Spectre DR optics on the carbines, and I'd
consider Swarovski for the bolt actions.
But Leupold is fine. And to answer the question again, yes - in my opinion the price of quality glass is always worth it.