I also have been having no success with pocketing Text.
For example: when the letter "A" is dragged into a rectangle, and then pocketing is performed, the outer line of the "A" is left as an island but the inner part of the letter is also engraved. No matter how you try, the inner part cannot be separated (ungrouped?) from the outer part of the letter and pocketed on its own. The guys writing this program are doing a great job so maybe this bug can be fixed in a later revision of LC.
Bruce