Alright, I've successfully used FontForge to create a copy of Consolas (although this should work with any font) with the bold style actually being italics.
These are the steps that I followed:
- Install FontForge. It's a lot easier to do this on linux than on windows/cygwin. I used a Ubuntu VM ("sudo apt-get install fontforge").
- Open Consola.ttf (the "normal" style font) in FontForge.
- Select Element -> Font Info.
- Change the Fontname, Family Name, and Name for Humans, all to the same thing. I used 'ConsolasVS'.
- Click Ok. Click 'Yes' to let FontForge generate a new GUID for the font.
- Select File -> Generate Fonts. Make sure you've got "TrueType" selected. Uncheck "Validate before saving". Click Save.
- Now open Consolai.ttf (the italic style font) in FontForge.
- Go back to Element -> Font Info.
- Change the Font names as before, and where it currently says "Italic", change that to "Bold".
- Go to the OS/2 tab, change the font weight to "700 Bold".
- Go to the Mac tab, change the style set to Bold.
- Click Ok. Allow a new GUID to be generated again.
- File -> Generate Fonts, as before.
Copy your two new ttf files into your \Windows\FONTS\ folder.
You can now have nice italic comments with Consolas in VS2008. Hooray!