Could you clarify who the "target audience" is? I've long wondered about the apparent gap between the universal anti-deathism the Lesswrong community ostensibly espouses and the blase attitude on display as to the affordability of cryonics.
My guess: many LessWrongers are students or relatively recent graduates in highly specialised fields, so while their finances may currently average pretty low, it is common for them to believe they will eventually become, if not wealthy, at least well-off enough to be able to afford the costs of cryonic insurance.
While I've never managed to get an exact figure from someone who is signed up - I cannot fathom why, and it mildly annoys me - the vibe I get is that it's expensive but not outrageously so, and easily affordable for an upper-middle class person.
For a lot of serious charitable causes, people expend tremendous resources on 'raising awareness' which probably, on net, accomplishes little or nothing for the cause it nominally supports. For cryonics, though, the technology already exists, the target audience can pay for it themselves, the main obstacle is genuine ignorance and perverse fear-of-death countermeasures.
The second problem seems intractable, but in the long term we can just let the blind idiot god fix it.
For the first, have any of the organizations involved considered saving up for, say, a superbowl ad? Or even just some youtube videos. I am imagining it set up as a conversation between two people in, say, an office. The skeptic brings up some plausible-sounding objection (sticking to the saner stuff), which is illustrated by cartoons with the continuing conversation as voiceover.
See, I talked to a relative of mine, who I respect very highly, on easter. She's planning to get cremated. Mentioned some technical objections which I know have been resolved, but which I couldn't adequately explain on the spot, and didn't know where to point her for the source.