While there certainly is a lot of 'fashion' and 'trendiness' in design, it's not all fluff. Skeuomorphism arose from a need to make highly technical interfaces comfortable and familiar. While it first appeared in the early PARC desktops, Jobs brought it to mainstream with the original Mac OS, with it's "folders, documents and trash cans." The heyday of skeuomorphic interfaces culminated with beautifully rendered interfaces for the iPhone where the goal was to make a very limited technical device be as simple, intuitive, straightforward and friendly to use as possible.

Along came better processors, larger screen sizes and more complicated 'non-modal' interfaces and what started out as familiar now became overly visually complicated. Too much 'edge detail' which took the focus off the main interface and just made it all look 'busy.' Thus the FLAT movement came along. With FLAT, you can put more controls and interface elements on a screen while still helping it to stay as clean, and therefore uncluttered as possible. Flat emphasized the use of color, icons and typography over rendered interfaces.

At first FLAT eschewed soft shadows and gradients, and any semblance of 3D. Now, UI designers understand the restrained use of drop shadows and gradients can be used to make controls easier to understand and access.

If I were to design a logo for MoI, I would first attempt to understand exactly what the client (Michael) is trying to communicate with the logo. I call this a Semantic Inquiry-- and I would use mood boards, discussions of products he admires (not necessarily software or CAD), and talk about his target audience.

We would talk about evolutionary vs revolutionary branding and help him decide what his brand means to users in this space. If Michael was interested in expanding his reach and becoming a first tier competitor to Rhino or Modo, I might suggest he consider the revolutionary approach and shoot for a more corporate design which communicates strength, power and simplicity with the possibility of appealing to a broader audience.

But, I somehow think he's more interested in a more artisan strategy, where he enjoys direct communication with a smaller group of his users and a more craftsman approach to new releases. In that case, I'd suspect an evolutionary approach would be better. Take the existing icon and 'bring it up to date' a bit. Allow it to read better at small resolutions but keep the colors, the cartoon look and whimsical style.

Next a round of concepts, then refinements, all focused on displaying the brand in likely end-use cases: Website, App Icon, T-Shirt, Business Card, etc.. Sometimes a good brand (IBM) had different logos for different size uses such as Paul Rand designed both a 8 stripe version as well as a 13 stripe version-- and this was BEFORE the Internet was invented!

I spent the last couple of years working with my friend Mark Rolston. As the former CDO for frog, he's worked on many big corporate identity programs and I was fortunate to see him design logos along with another good friend, Sir Charles Hurst. While both have different styles, they also both use a similar process as the one described above. HTH.