Everyone, thank you for your comments. I really appreciate it.

Ultimately, even though I don't think I'll ever give up riding steel, I must admit that I had more fun with index rather than friction shifting, based on my experience touring on a 2012 Trek 520. Sadly I would much rather trust my life on a mountainside to index shifting. These Modolo brakes are no longer acceptable as well, and needing a new freewheel or drive train, and having just bought a new headset... it makes me think it's just time for an overhaul. For that overhaul I need to know the right direction to go so that it doesn't fall into obsolescence, and your comments have been useful for that.

In my heart I just need to answer, do I really want to spend a ton of money on keeping this bike going forever? How much like a modern bike do I wish it to be?

The answer to that is, I want this bike to live up to its fullest potential for what it can do for me, and in order for me to be comfortable descending mountains again the shifting has to become modernized, and it has to brake significantly better. That means spending a bunch of money. So I might as well just make it a project and get a group of parts. It taught me a lot getting to this point, and now I think I know what I want better.