I'll apologize in advance if this is largely a duplication. I posted here earlier and it appears that the forum ate my post. Damnit. But I'll try to recreate what I wrote earlier - eleven suggestions for Expressive development.
I'll begin by saying that I approach this project from a couple of perspectives - I am a FreeHand user. I use Illustrator because I have to, not because I want to. I worked for Micrografx for six years, where I did user interface design for Designer, Windows Draw, Picture Publisher, et cetera. And lastly, I worked for Altsys as the Senior Product Manger for Virtuoso, the version of FH that was written for Windows NT, Sun Solaris and NeXTStep.
My first wish for Expressive would be that they start with the basics. The worst thing about Illustrator (and the best about FH) are the Bézier editing tools. Illustrator (specifically and generally) makes me jump through hoops to do ANYthing. FreeHand is easy, streamlined and intuitive. Get that part right FIRST. Build on that foundation. It's not enough to be able to draw/edit Béziers - you have to make it frictionless to do so.
Second: Prioritize. I could care less about 3D and the perspective grid. Prioritize which features are needed by the most users and get them right first. There's always time for upgrades later. But if you don't get the priorities straight it will cripple the program.
Third: Get user feedback early and often. Macromedia was big on this. I served on two "expert" panels - one for Fireworks and the other for Freehand, where they'd bring us in under NDA, open the kimono and show us cutting edge stuff to get our feedback. Adobe doesn't do that. It's a great idea. Letting users help you prioritize features is not a bad idea either - just remember that these results can be skewed by too many "hot" features, and give you a false sense of urgency, leading you to overlook the bread n' butter features.
Fourth: Don't fall into the trap where you start to believe that, because you understand development, you know more than users do. Users may not know - or care - how to code a feature, but they know far better than you how they'll use it.
Fifth: I'd LOVE to see you build Expressive as a modular platform, where EVERY tool and feature is, essentially, a plug-in. This would make the program lean and mean for those who don't need certain features, and rich/deep for those who do. It would allow users to customize the app for things like technical drawings, pre-press, and web design.
Sixth: Make sure it's a Rosetta Stone for file formats. I desperately need to be able to open FH11 and FH10 files. But I need to read and write AI, EPS and PDF formats, too. That's a BIG DEAL for me.
Seventh: Take advantage of today's APIs. My most frustrating FH experience is a lack of mouse scroll wheel support. Maddening.
Eighth: Don't romanticize FreeHand. It had flaws. Many of them. In particular regarding the U/I, think like a USER, not a PROGRAMMER. I don't care that applying a Postscript fill is programmatically an entirely different thing that flood filling a shape with a color. To a user, a fill is a fill is a fill. Group items in the U/I according to USER needs, not for the convenience of a software engineer.
Ninth: Get rid of the obsolete features. Does ANYBODY care about Flash support in this day and age? I wrote two books on Flash and I couldn't care less.
Tenth: Git 'er done! Let's not wait until you have every feature from FH11 done before you ship. A good plan today is better than a perfect plan next year.
Eleventh: THOU SHALT NOT PORT. I have some inside knowledge on the folly of porting software from one platform to another. Please don't write this for Windows and then take the easy way out and port the code to Mac with some translator. Each platform needs to be developed as a native application.
Those are some pretty broad brushstrokes, but that's it. Do these and I'll be first in line to buy.