As I started learning more about theory and applying it to music, I felt increasingly that the RN's had usefulness in particular contexts, but music is more flexible than that.
I didn't realize the Roman number chord analysis came from mass education in the 19th Century. I had just assumed it had come from centuries of doing it that way. TIL - today i learned, and all that.
I think it's pretty obvious that figured bass had nothing to do with Roman numerals. So from that we can probably intuitively figure out that Roman numerals came later, and that's exactly what happened. But I am mostly concerned with the insane idea of combining Roman numerals with figured bass. To me that puts us into a system that gives us the worst of two worlds.
That's a tough question to answer. I only use Roman numerals, when I am teaching, for very general concepts. I never use them for myself. For example, if I am in the key of C major or C minor I am aware that C is going to make some sort of I chord, F is going to make some sort of IV chord, and G is going to make some sort of V chord. If I have a G7 chord I'm going to think of that as a V7 chord. But I'm not thinking those numbers. I'm just thinking that those are my go-to chords for the key. The music that I prefer and the music that I compose is generally very chromatic, so I think about what key I start in, what key I am currently in, and how I am eventually going to get back to my starting key. I always know where I am and I always know why I am moving to where I go next. Roman numerals just get in my way for anything that is complicated or sophisticated.