Windows as opposed to Linux, MT vs. Wordpress

Firstly, MT is what I’m used to. As of the middle of next month, I’ll have been using it for 2 years - whereas I’ve been using Wordpress for less than 3 months. It’s the same reason why I use Windows as opposed to Linux - sure, Linux may be more secure and less likely to crash, but I know how Windows works and I feel comfortable in that environment. Neil's World: Why I'm not switching to Wordpress

Makes me think of that other post about MT. But I understand the warm glow of familiarity – how best to replace it? My vote is to win people over through better features and better usability. How much better does another solution have to be to win people over (because "different that what I'm used to" can be a large block)?