I think the fastest way is to play in the chords with MIDI detect or audio detect.
I was just working on Giant Steps and Blue Bossa and found it best to play in the changes and then go back and improve the voicings and voice leading. Scaler does come up with some odd enharmonics, but those can be resolved with a few clicks. I’m still new at this myself, so don’t have any best answers on this. I’d like the Circle of Fifths to have Flat Notes, but, development takes time.
Anyway. I also like the chord editor. If the chord name is wrong, but it’s the right chord, I let it go. I don’t care if it says A#7b9. I know it’s a Bb7, and you can click the scale type for enharmonic equivalents, but not C Major.
I think I’ll develop a workflow with Scaler and these sort of things will just become part of how this tool works. If I come up with any “killer tips” on this, I’ll post about it. Maybe someone else will share a few good ideas or suggestions.