The first is that the unusual capitalization and pronunciation are a barrier to new users. I've used macro packages in the TeX family for about four years now (though it seems much longer! I can't believe for how long I was putting out such ugly papers!), but I'm now consciously trying to remember to pronounce them as tecks, latecks, zeetecks, conteckst, etc, and to type them as Tex, Latex, Xetex, and Context (outside of this message/forum). The odd capitalization doen't win fans among people who appreciate typographic tradition, and the pronunciation requires that, instead of explaining first how powerful and useful these systems are, one explain the Greek chi and Donald Knuth. It doesn't give a good impression when one's first exposure to TeX involves being told one is wrong in how one pronounces a word that is less than 40 years old (The same goes for many open source projects). Further, if the name is brought up in conversation and piques the interest of a potential user, they will have a difficult time later searching for it when they type in contekt or conteckt.

The second problem with the ConTeXt name is its shared spelling with context. When I google context and font, I get so many pages imploring me to consider the context of my document when choosing between Arial, Times New Roman, and Comic Sans. Many of the things I'll be searching for while using ConTeXt yield thousands of irrelevant pages because of how context can pop up in so many topics that share major keywords with the typesetting process.

Of course, I myself am in no position to advocate a name change, and if the two issues I listed are the price for having a cutting-edge typesetting system, then I'm still a pretty happy camper. But if any of the people who have actually worked really hard to put this together have ever thought about bringing up a branding change, here's my two pence.