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The Flat Keys
Guitarists live in E, A, D and G, because those keys have open strings in them. Jazz lives in F, B♭, E♭, A♭ and D♭, because those are comfortable for horn players, and horn players wrote the repertoire.
There is no way around this. Call a standard at a session and it will very often be in a key with three or four flats in it.
The good news is that guitar is a transposing instrument by construction. Every voicing in this path is movable: no open strings, so the same grip works at every fret. A ii-V-I in C and a ii-V-I in D♭ are the same three shapes, one fret apart. The difficulty is not physical, it is that you have not practised naming the chords in those keys.
The circle of fifths is the tool for fixing that. Neighbouring keys on the circle share all but one note, so working around it one step at a time is the least painful way to cover all twelve.
Circle of Fifths
Start at C and work one step at a time. At each key, name the ii, the V and the I out loud before moving on.
Now play in one. This track is Girl from Ipanema in D♭ — four flats, and a key most guitarists would rather transpose away from.
The ii-V-I in D♭ is E♭m7, A♭7, D♭maj7. Two of those three are grips you already own: the E♭m7 is the minor seventh shape from lesson one and lesson three, and the A♭7 is lesson one's G7 shape moved up a single fret. Only the D♭maj7 is a new shape. Find them and play the pattern from lesson four over the track.
One thing that will look odd: the chord charts and the changes panel spell this key with sharps, so what a real book calls D♭maj7 appears as C♯maj7. They are the same chord and the same fret — the two spellings are just different names for one pitch.
E♭m7
E♭m7 — the ii. The same four-string grip you have been using since lesson one.
A♭7
A♭7 — the V, and lesson one's G7 shape one fret higher.
C♯maj7
The I, charted as C♯maj7. A real book would call it D♭maj7. Same chord, same fret.
Girl from Ipanema - in Db (120 bpm) - Backing Track
Girl from Ipanema in D♭ at 120 BPM. Bossa pattern, flat-key shapes.