In the first case, easy enough today, I could have an agent in about 30 minutes who would sell you a policy and wait for it to be valid until the payment came through the chain, no issue.
In the second case... far greater issue. Insure that the chain will stay intact? Insure that you will not be scammed by some flaky alt-coin or fly-by-night exchange and snake oil dispensary? Too many variable, and too many additional opportunities for the criminal scumbags who lurk in this world to create their instant web identities and rip people off. Trust is a mighty rare thing around these parts, and it is most often abused.
Perhaps what it needs most is a bump from something legit, an article in the WSJ, a breakthrough into more mainstream media, again, and go for the bounce that happens when the new adopters flock to it, and filter in the next generation of users.
I do mean insuring BTC. I actually posted a thread about an interesting idea I had about creating a business acting sort of like a BTC reserve (like a BTC fort knox). The value of this business, as it acts as a reserve, would constitute backing for BTC, and it's assets could be insured federally.
The business would have a triple role as a BTC reserve, a mining pool/company, and a computer/GPU manufacturer and retailer. People could donate old rigs/GPUs to the company and they would be used either 1) to add to the Business mining pool. The company would essentially a massive mining farm and donators could receive a share of the pool. Or 2) the materials would be used to create new rigs/GPUs for retail. The idea is to tie BTC value into something that is integral to it - computers!
So, again the 3 roles of the business would be...
1) Act as a BTC reserve by associating the company value with BTC backing value. This value is established mainly by the computers being sold and used to create BTC. This seems to make sense since not only are the computers doing the work, but the computers confirm the value of BTC through the Bitcoin client. No computers = no BTC value due to 0 confirmations.
2) Act as a mining pool/company. It would use some of the donated material to run a mining farm. Donators receive a share a the mining proceeds.
3) Act as a computer manufacturer/retailer. The rest of the donated materials would go toward financing new computers and GPUs to be sold and used for mining. Not only does this create a nice little cycle (i.e. create, sell, mine, donate, repeat), but it would establish the company as a business. The company value could be insured, and this would be a nice little backing for BTC.