@threearmedcow
The rating in Strawberry is from 0.0 to 1.0. A half star is 0.1. So 5 stars would be 1.0.

There are no standardized tags for rating. How the rating are saved to tags depends on the audio file format and the software.
One software can behave one way, and another can behave very differently when it comes to ratings. Another software might use an entirely different tag, and save ratings differently.
So comparing software to see if the rating of stars is read correctly don't always expect to see the same result.

However, when I see you mention some numbers with "192" and "255" I'm only guessing that it could be the POPM tag popularimeter frame for ID3v2 which are not really ratings, but commonly used to store ratings. These are saved by Strawberry too but converted from the rating, 192 should be converted to 0.8 (4 stars), 255 should be 5 stars.
I think it's mostly the same as described by wikipedia. See: https://en.wikipedia.org/wiki/ID3#ID3v2_star_rating_tag_issue
Another software might convert these differently though. So might treat both 192 and 255 as 5 stars. But it's hard for me to answer for another software I have no knowledge of. And you don't even mention what audio file format it is. If you saved the rating with strawberry for both files, I'm not really sure how they could be saved with different values.
Other formats that use Vorbis comments uses very different tags, does not have standardized ratings tag either, and no POPM tag.

For MP3 ID3v2 Strawberry saves a "FMPS_Rating" with the 0.0-1.0 rating too.
I found that Strawberry was writing the FMPS_Rating for MP3 but not reading it back, so it was always converting the POPM tag. Should be fixed now, so if the FMPS_Rating frame exists, it will use that instead of the POPM for rating, which will be more accurate for use in Strawberry. But the database rating will take priority, so if a rating exists in the database for the song, it won't re-read it from the tags.