Flexi and/or Illustrator

Since you already know Illustrator, and apparently like it, your needs are probably better served with a product like CoCut Pro. This will add much to Illustrator and serve your needs 99+% of the time for a lot less money.

If you were asking which of the major signmaking applications to get, I would likely recommend Flexi because it is very much like Illustrator on steroids ... and again, you mention familiarity with Illustrator. Flexi is probably a bit more productive than CoCut/Illustrator and automates some tasks like special effects while remembering them if you wish to change their parameters at a later point. You would have to decide if this is a good choice for you.

 

If all you're doing is cutting vinyl graphics for banners and other smaller types of signs then CoCut or other bridge programs may work perfectly fine for your needs.

I would recommend an application like Flexi if you're going to do designs for larger scale projects, such as billboards, lighted signs, etc. You can design just about anything at full size, even a huge building elevation. The CAD style underpinnings of the program allow for this. Freehand and Illustrator can't hold drawings any larger than about 226" X 226". There's some sort of floating point issue that creates that limit. Corel will allow page sizes as large as 100' X 100', but it is not a Postscript drawing program like FH and AI (and its color handling isn't as good either). Flexi also interfaces directly with routing programs like EnRoute.

In short, I would recommend a dedicated app like Flexi if you plan on designing and manufacturing more permanent commercial and/or lighted signs.

 

I design all my stuff in Illustrator and Cadtools (www.hotdoor.com) and most of it is large commercial signs and large projects. I do have Flexi-Sign too. I recommend it for it's great production capabilities, especially a larger sign shop. I never design in it....I used to, but with presentaions and going back and forth into other programs, Flexi is a pain.