Hi Meredith,
I would have everyone install the font the exact same way, and get rid of the other version completely. Even though the name is the same. the FOND ID is likely different. The FOND ID is a social security number for fonts. So even though the names are similar, consider them to be 2 entirely different fonts (like identical twins, but they are not the same person). 2 options I know of are:
using fonts.adobe.com
installing from google fonts
This is a free font from Google fonts, and they did some strange things of making 3 versions of the fonts without any explanation.
I do not like this having 4 groups for the same fonts. It clutters and lengthens your fonts menu without any explanation. There is font hinting and such to not have a need for fonts design at specific sizes, so the creator of DM Sans has created a font that causes more confusion and problems untles you all install the same fonts. Get rid of the extra one you do not need, like a virus, it will just cause you all repeated troubles.
Jeremy,
You should probably start your own post as your probelm is with different fonts. Thanks for screen shots, but could not follow what you started with and ended up with.
 
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