For entrepreneurs, money talks. For users, convenience talks. For investors, returns talk. Everything else is water under the bridge.
I like your perspective. So for each group, what would be the most compelling strength or misconceptions/obstacles for adoption?
I like this perspective too. There are many ways to tailor the message depending on the demographic you are pitching. Try not to cross the streams too much, it can confuse the message.
IMO one of the biggest obstacles to overcome is reducing the cognitive dissonances of voting i.e. making it easier, more intuitive, less time consuming, etc. I like the ideas luckybit mentioned before about making AI algorithms in the future that could vote similar to how you would vote, automating it. Allow manual overrides of course. Then you could just glance every so often to see if your AI voter is sticking to your voting ideologies.
On that note, everyone vote for dev-pc.bitcube! Bitshares can use all of the active developer delegates it can get.