I'm not at all an expert, just a listener. But I'd recommend jumping in the pool and splashing about. Your ears will tell where to go.
I try not to get caught up in understanding the words -- at least at first -- because my understanding of German is sketchy, at best. I just try to absorb the music, the stuff beyond language. Afterwards, I usually circle back around to translations of the lyrics, and that offers another sort of meaning. ... At least that's how I make sense of them -- definitely the music first, then the words.
I've discovered that I tend to be drawn more to female lieder singers -- performers like Janet Baker, Elly Ameling, Brigitte Fassbaender, and Margaret Price. The color and heft of each of their voices are very different, so each of them will be more or less suited for different types of songs: heavy/tragic, lyrical/pastoral, romantic, or whatever. ... One male singer recommendation -- for all German lieder, not just Schubert's: Hans Hotter. An amazing voice.
Next up for me, prompted by this Schubert talk:
Another excellent entry in Hyperion's series.