Working with a MIDI file and without much grounding in music theory, I had and have no real way of determining whether to represent notes flat or sharp. I consulted several people and generally got a response of "Oh, interesting stuff! It's not clear how you should transcribe that."
I'm still interested in opinions! If you want to check it out, the score is here: https://musescore.com/user/36584999/scores/7810499
- Match the type of accidentals used by the key signature.
- Use sharps when the melody is moving up, and flats when it's moving down.
- Use whatever accidentals give you a visually pleasing spacing of notes in "thirds" as represented on the staff. (As advocated here.)
- Use the accidentals that are physically compatible with other notes in the chord. (Only a concern for certain instruments, but e.g. I understand that the pedals on a harp affect many strings at once, so playing a particular combination of notes may require a clever approach to the pedals, indicated by what might otherwise look like an unnatural set of accidentals. This wouldn't apply to a piano, where G# is just a separate key from G, not a modification of the G key.) I think this is what you're going for?
But I guess you could get the flat 5 if you did the tritone substitution of the secondary dominant of the IV, which would be bV7.
And then I think you may be talking specifically about measure 11. I'm pretty rusty on my analysis, but it seems like it's the iv7 chord, but starting and ending with a chromatically raised root, which is slick because it acts as a passing tone from the i chord in measure 10 and the V in measure 13. I would probably do Gb -> F -> Gb, because the F is the chord tone, and the Gb is the nonchord ornament. But yeah, probably doesn't really matter!
There can be only I.
I, bII, etc. are chords not pitches. II-bII-I is a chord change. Pitches may go up or down and voices may go away or arrive. They may be part of those chords or not. And there may not even be a root pitch.
Or if you want formal theory, chords are scales [1] and there ain't no such thing as a scale with a sharp I. If you sharp the one it’s a different scale starting in a different place.
The b in bII is not an accidental and bII is how to communicate the chord in passing. I/bII is also possible to communicate a modulation (as would be vii/II, etc. if the modulation is elsewhere).
There are “enharmonics” for chords that aren”t the root of course, e.g. #IV and bV depending on intent, convention, or playability. But #I will be marked wrong on the entrance exam and only raise you standing among an avant guard that isnt accepting new members.
[1] see Russell’s Lydian Chromatic Concept.
It depends on what's the function. If you want to use the tritone-substituted G7 to modulate to the sharp fourth, you'd write it C#7 and resolve it to F# (or F#-).
The Roman Numeral analysis would be V7/#IV if you are modulating in C. And something else if you aren't in C. Roman Numeral Analysis is independent of key or tonal center. The Roman Numeral Analysis would be bII if you are not modulating because that's how Roman Numeral Analysis communicates.
Thinking about Phrygian mode. The two is always a bII.
{0} As an aside, in The Common Practice the bII is often notated N6 (for Neapolitan 6th) to set up a perfect cadence, i.e. I-N6-V-I.