Font family weight not displayed?

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Font family weight not displayed?

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I've been trying lately to get a small, OT family with two fonts (Regular and Inline) to work right but I've been running into roadblocks. My questions are threefold:

1. In order for the inline version to show up, I have to change it to another basic font weight (other than Regular) in OS/2. Is there any way I can keep the weight for both fonts as 'Regular' but still keep both of them in a font family (e.i. without generating them as separate fonts altogether)?

2. When I go ahead and generate my font family as described above (with the first one designated as Regular and the second one designated as Medium), the second consecutive font installed will not show up. In other words, when I download Regular first and then Medium, the Regular weight is the one that shows up in Window's Fonts and vice versa. I know the second font does get installed successfully since I can open up Illustrator and access it just fine. The thing is that Window's Fonts doesn't let the second installed font show up unless I delete the font that was first installed (ex. deleting the 'Regular' makes 'Medium' appear and subsequently take it's place.

3. Is there a way that I can group the fonts into a built-in folder so that it doesn't show up as a font family occupying two separate spaces on the list but rather a font family that has a folder with the family name on it and can be clicked on to reveal the family's fonts?

Any help or insight on these things would tremendously appreciated.