We have Flexi 7.6, Illustrator and Photoshop CS2.
For vinyl jobs I design in Illustrator and cut using the FineCut plugin that came with our Mimaki plotter.
For a print job, if I need an image, I edit that in Photoshop and 'place' it into Illustrator. If I need a rastor background that would get designed in Photoshop and placed in Illustrator where I'll add the text. (I guess that's a holdover from my prepress days. Whether or not that makes sense anymore with Photoshop's vector abilities, I don't know.) The file would then be saved as an .eps and opened in our Onyx RIP.
Sometimes I'll design in Illustrator and then open or place it into Photoshop and do further work from there. Save a layered file, (I always save a layered file for future editing), then flatten it and SaveAs a .jpg and open that in our RIP.
If the scale of the work goes beyond Illustrator's limit I'll do that part of it in Flexi which enables me to get measurements. At times I'll design the text in Illustrator and save it back to version8 and open that in Flexi, (which always converts it to outlines), for scaling. Other times though, I'll design the text in Flexi, and then save it as an .ai file, (which always converts it to outlines), and then open it in Illustrator and go from there. It depends on what I'm trying to accomplish.
For me, I like Flexi because it's sign making software and offers a ton of features relating to working with text an easy task as well as some great, and I mean great, node editing tools. But the low screen resolution and the odd, huge cursors drive me nuts which is the main reason I like working in Illustrator whenever I can; so my design looks crisp on screen and where I am fully confident in its node editing tools and on screen color accuracy.
I can't seem to get a grip on managing color effectively in Flexi. Being an Adobe person I've never delved deeply into Flexi's color abilities.
Your question, "And why the crap can you not outline text properly without having to convert it to outlines thus making it uneditable?!", is undertandable, if, as I assume, you are referring to adding an outline for vinyl cutting. Flexi is sign making software and geared to vinyl cutting. So if you add an outline it is added as though it expects the design will be cut out of vinyl. Illustrator is illustration software geared primarily to printing. So if you add an outline it is done as though it expects the design to be printed. That's two very different animals right there.
There are tools and methods in Illustrator that can accomplish what you are trying to do which is convert a print file to a file appropriate for cutting vinyl. To some these methods may seem like jumping through hoops to get the same result that Flexi gives you without the extra work, however, one must keep in mind that Flexi is made to cut vinyl and Illustrator is made for printing. It seems using either for the purpose the other was designed for creates some headscratching at times.
It all comes down to which software you've spent the most time with and have become comfortable in understanding how it "thinks". Personally, I wouldn't trade one old copy of Illustrator 8 for a truckload of Flexi or CorelDraw or Freehand (do they still make that?) or Gerber (whatever their latest and greatest is called), There are others who would use that Illustrator disk for target practice and think nothing of it.