I didn't really care for soloing that much since I'm usually improvising a line anyway playing the changes. It's only the past few years where I've felt comfortable with soloing and I'm still learning. I have improved with looking ahead and seeing patterns in the progressions where I don't have to stop and think about every single chord. A little music theory is a big help!
I had a light bulb moment about 20 yrs ago with jazz. At the jazz camps, the staff was always talking about ii-V and ii-V-I progressions and how important they are but no one really explained why. Then I was playing some tune and realized I knew the next six chords without really thinking about it - a series of ii-V changes. Then I found I could generalize that even more across more measures depending on the tune of course. Then there are some tunes where the chords are "too close together" for me.
"All The Things You Are" is a great example of ii-V progressions. I also call this tune "All The Chords You Know". Here's a pretty good analysis of the tune:
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