Unless you have a very small bit 1/16 or less you will not be able to carve the letters/text correctly, whereas if you have a 60 Degree or even a 90 degree v-bit using the V-Carve Toolpath may work better for you of course then it is all a matter of what you are trying to achieve.
Example: The "E" you were trying to pocket. The upper left and bottom right there are small areas of the vector where a bit would have to fit into in order to carve them correctly. Now on the other hand if you were to carve them as raised text/letters then yes after carving out the lot of the material with a large endmill (.25") and come back and profile cut the letters/text with a .125 or .0625 end mill.
The type of text and its size tends to lean more towards a V-Carve Toolpath.
If you are dead set on pocketing then I would suggest that you come back with a profile pass on the inside using a v-bit which would clean up those small areas but the downside to this is it adds a slight beveled edge to the text/letters.
Just my opinions and thoughts!
BTW -- the "B" in Boat is an open vector it will need to be a closed vector in order to use the V-Carve Toolpath on it.
Oh and checked for stray vectors ---- There are NONE!!!