1 - You will have a greater selection of fonts that way. You can use any font installed on your computer so you basically have a limitless supply of fonts (can find many online to download and install very easily).
2,3 - That font she selected is very hard to carve with anything besides a v bit. It will only carve those tiny black lines that outline the letter. If you want to use that font you will need a TINY bit or use a vbit (F-Engrave is free to use software).
4 - V bit if you go that route or a flat end mill.
5 - You can signup for that feature with this link: Two stage cuts - #1019 by MikeJeffcoat . Just reply to that thread saying you want to try it out and usually within a day it will be added to your account. You’ll then be able to pick a bit for roughing and detail.
Summary: If you want to use that font, use a v bit and v bit software (or tell Easel your vbit is .001 wide or something. I haven’t had any experience doing this but many others have done it). If you can change fonts, redesign it in inkscape (or use one of Easel’s fonts) and import to Easel as a svg. Easel will then tell you if it can cut that font with the bit you have selected.