For what it's worth...
As I see it, the problem arises because there are three pairs of keys that are enhamonically equivalent.... that is, where key signatures can be expressed either as sharps or flats. (All other key signatures are unique events.)
The key signatures that have flat and sharp equivalents are Cb/B, Gb/F#, Db/C#.
If a song is notated in one of the above keys, and a problem exists in notation, try changing to the enharmonic key and see if the problem is resolved. For example, if the song is in Gb, change the key signature to F# and see if that works. (The problem that arises with this solution is that some people prefer to play in flats rather than sharps.)
As an experiment.... I just created a short progression in Gb (Gb, Cb, Db7, Gb). On the chord sheet this was displayed as Gb, B, Db7, Gb. I transposed the key to F# (pitch equivalent of Gb) and the display correctly read F#, B, C#7, F#.
Also...
When I converted the Gb display to Roman Numerals, it correctly read I, IV, V7, and when I converted it to Nashville notation it correctly read, 1 4 57 1. (It was not necessary to convert Gb major to F# major.)
Not sure that this post solves anything... I just thought it was interesting

Noel