V-Carve pro comes with a few single line fonts (15-20), but I've never used Cut 2D. You'll need to download the demo and spend 5 minutes to find out if it has any. I have a feeling it doesn't, based on what I just read on their website.
ttf to .dxf won't have any single line fonts, as it converts True Type fonts, which are not single line. Afaik, it's been $100 for at least 10 years.
Do you need a CAD program to clean up and customize Cut-2D? (Vectric stresses lack of design ability with Cut-2D)
Not sure what you mean by clean up and customize. I believe that Cut 2D can only draw rectangles, and circles, or ellipses. If you need to draw other shapes, you need another package than can export in a format that Cut2D can import. You might want to look at Inkscape, as it's free. If you do use Inkscape, you'll want to download a better .dxf exporter than the built in one. This one is supposed to work good.
http://www.bigbluesaw.com/saw/big-blue-saw-blog/general-updates/big-blue-saws-dxf-export-for-inkscape.htmlWhat CAD programs do you use with TTFtoDXF?
Any program that opens .dxf files should work fine with it.
If you have BobCAD, it should be able to do everything and more that Cut2D can do. I would think that it can also do V Carving, and convert ttf's to vectors for machining?
Does Cut-2D direct output and Mach3 play nice?
Yes, all Vectric software works very well with Mach3.