I have and use two Milescraft products, the Signcrafter (I think it's called) and the Pantograph.
What I don't like about the Signcrafter is that you are limited to the font that is offered, although in 2 sizes, upper & lower case, plus numbers. But it is fairly easy to use and is consistent. The Rockler version requires attaching each letter individually. I haven't used that system but it's probably very similar. The Signcrafter sets up your letters in a fixed "track".
The Pantograph is basically unlimited as to font & size but has a little more of a learning curve than the Signcrafter.
I, as well as several people I know, also make signs freehand and there is a guy named Dave (?) who has a lot of YouTube videos about freehand sign making. A light may be helpful but really is probably not necessary. Maybe a clear (v. black) baseplate on your router also helps.
While making signs these ways is kind of fun to do, the CNC has, in my opinion, largely taken over the sign making process. So this is a whole new world for making signs with skills to learn, equipment to purchase, etc.
There are several options for bits but I generally prefer the chamfer or pointed ones. Whatever you use, you don't need to go as deep as you probably think that you need to. It's a lot easier to go back over a little deeper than the other way.
Hope this gives you some directions to take a look at.
Last edited by Red Stick; 12-17-2018 at 05:32 PM.
Reason: clarification and additional information