Before you accuse me of being arrogant: I feel like I should be mature enough to start listening to "real" music (e.g. classical) by now, but I find that it's too far over my head. So I think I'm in a musical "limbo".
That's one think I like about older blues. Many of those classic blues musicians still had to work to pay the bills, had families, and were never going to be pop stars. It's people singing about how tiring work is, how complex married life can be, and what it's like to worry about paying bills and just getting by to the next day. They sing about getting older and being less energetic and passionate than you once were.
The funny thing is that I only listen to blues on the radio at night when doing some errands, so I couldn't name a single artist I've listened to. But sometimes sitting in a parking a lot, just after turning the ignition, you realize you can let the ice cream melt just a bit to take the time to hear someone else sing about troubles that are ultimately not so different from your own.
It took me a while to be able to really get into it, but without Bill's explanations and enthusiasm, I would still be lost. His fantastic voice is icing on the cake.
I think anyone could likely find a trove of new (to you, at least) content by simply digging a bit outside of their comfort zone to try genres that are totally alien to your ears, like Avant Garde Jazz or Krautrock or Experimental music, just for example. Or by finding a genre you know you like, then exploring the likely myriad subgenres which emerged years later or are developing right now under its influence. A lot of the most satisfying things in life won't be fed to you, so the most important thing is to just keep an open mind and appreciate that although certain things may not click right away, it may not be worth writing off entirely. An important aspect of appreciating contemporary music is being aware of the cultural canon from which it was born and finds itself released within. I find that being able to connect some dots in one way or another between older and more contemporary artists/releases/genres will yield a greater appreciation of what's happening today. Applies to all forms of art, really.