Merging/Union Causes Offset path result to disappear in part

[Boldline]

In this attached example, I had taken the original wording and gave it an offset path. I removed the original words temporarily while I selected the offset path I just made and tried to merge/union it into two separate main shapes (top and bottom shapes)
Each time I attempted to merge or union, parts of the offset path shapes would disappear.

The issue may be with the initial font used, but even still, VS needs a solution for troubled expanded fonts lol. I zoomed in on the result of the offset path and noticed some odd results (see pic below) I do know ofr a fact the font is not perfect in it's construction.

File is attached here:
0_1637632565862_Boonville Wrestling2021 Green Shirt2.vstyler

[VectorStyler]

@Boldline I got the file (found the font also). This one will take some time to figure out.

[Boldline]

@vectoradmin You mentioned you found the font - but for the sake of being sure on it's name, it's called "Sports Headline". I can email you an otf file if that helps