A: Yes, in both Silhouette Studio and Design Space, you'll need to type your text in all Uppercase to get one half of the font. Then, type your text again in all lowercase, to get the other color.
If a Wizard user reads this, you can type your text, then click the font flyout at the top of your Wizard and click the 2 at the top. This will change the font into the 2 color font automatically.
Whichever software you use, be sure to also size the font so that the holes measure .135" if using ss10 rhinestones.