I don't think it's worth pursuing bizarre legal hacks for a couple of reasons. One is that regulators and the courts would simply ignore what you've done there and assert you are still a securities issuer. That kind of flexibility to avoid loopholes is both the power and the danger of law.
I'm not convinced that "bizarre legal hacks" cannot work. Shell corporations, offshore companies and trusts also can be seen as "bizarre legal hacks", but they are widely used and are quite legal.
For example, it is quite obvious when offshore trust is used to pay less taxes, but still it isn't illegal to do it even when intent is crystal clear. E.g. this:
http://www.bloomberg.com/news/2012-09-27/romney-i-dig-it-trust-gives-heirs-triple-benefit.htmlSo, well, why not use same kind of hacks which financial industry uses now for decentralized markets too?
For example, something like this:
http://en.wikipedia.org/wiki/Orphan_structureUse of offshore trust can effectively decouple questions of crypto-ownership (which can be handled in jurisdiction which will recognize crypto-ownership as legitimate) from questions of company operations (it will still be subject of local laws).
Offshore financial centres will likely be much more friendly to new technology and new concepts than more financially conservative countries