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Here's a fun bossa nova song we can look at. Let's talk about one or two considerations. The intro, verse tag and outro is based on 4 chords

Cmaj7 - Bb13 - Abmaj7 - F/G (or Gb13 in the intro)

The very intro is a little different as it sets up the verse melody via a Gb7(#5) chord. But let's talk about how we might think about improvisation when faced with the main chord sequence. How might we simplify this? Don't forget, deconstruct whenever possible.

OK so the main verse is a pretty simple melody. I don't need to talk about that. So back to soloing over this. The sequence starts on Am7 and shifts up to a Cm7 chord. You can think of The Eb/F in the next bar as an additional chord of Cm7. The next two chords are Gm7 and Bb/C. Again, in your mind, substitute the Bb/C chord as an additional Gm7 chord. Thinking this way gives you more space to play on one chord. The next chord is Dm7 and over the course of the next 4 bars gets us to Bbmaj7. I would therefore not worry about the Ab/Db passing chord when soloing and simply think 2-5-2-5-1. So in your mind you would be playing on Dm7-G7-Cm7-F7-Bbmaj7.

The Bb7(#5) chord is a tricky chord and it may take you by surprise so be prepared for it. Dominant 7th sharp 5 chords always indicate augmented melodies so it wouldn't hurt to simply outline an augmented triad at this point. You can't go wrong. Then it's a relative minor turnaround into Gm7.

2-5-1 into a minor chord such as Gm7 is often prepared diatonically by making the 2 chord half diminished. So, instead of the sequence going Am7, D7, Gm7, it more correctly points to Am7(b5), D7 and then to Gm7. There will be exceptions but this usually holds true. Relative minor turnarounds are interesting as you can play the same lines as you could on the relative major. The relative major turnaround would be Cm7-F7-Bbmaj7. Try it and see for yourself.

So where were we? Yes, two five into Gm7, followed by D7(#9), a pivot chord. This chord seduces us into thinking that we might go back to the key of Gm7, but no, it surprises us when the sequence goes back to Am7 to begin the verse over again. It is little surprises like this that allow the soloist to sound more interesting than he or she might, simply because it is the harmony that is presenting the surprise, dictating what we play, not the other way around. I think this may be one reason I am so obsessed with composition. Surprises in arrangement are intoxicating!

So the sequence repeats again and there is a tag just like the intro that repeats twice. The outro is once again that four bar tag that goes round and around and because the sequence descends the way it does, enables the soloist to build and build, without actually having to say too much.

There might be two ways to look at the outro and verse tag. One could think of the 2nd chord of Bb13 and think Gm7 instead, when soloing. This might present some easier ways to approach it. Target the 3rd chord Abmaj7 in your mind because you will need to be prepared for it when it comes. It's a little left turn. But I'll be honest, when I play this outro sequence, I actually, for the most part, just think of chord tones. I am simply outlining the chords and resolving back to C major in the most musical way I can think of.

Have fun with this.