I suspect that the maintenance hassle is just too extreme for any "regular" user to want to use this service, when the M-of-N solution is so comparable and so much easier.
Sure, for people who tend to churn through 100% of their savings regularly (ie. they don't have much savings), this type of service would be useless. I'm more thinking about someone who has a large sum, say $5M or something, stashed away, and they might have $500k in their own accounts for their spending. The pre-signed transaction ensures that their windfall can be passed down. They wouldnt be touching this money and spending it every day. Also you could break the $5M into $1M chunks so that if you had to break one of them, it only invalidates one of the transactions. For the $500k wallet, you could use an M-of-N strategy so that the coins don't get burnt if you die. In my opinion it's weaker security, but I guess that's debateable.
Also I'm thinking long term. Like, in the future if bitcoin is mainstream, everything is going to have to be really easy to use. Hiding away files in safe deposit boxes and having agreements with lawyers is going to be too complex. Potentially a multi-sig type of service, with an easy web interface and appropriate wallet support, could make it really easy for people to manage.
I appreciate your thoughts as I hadn't yet thought about the fact that there might be simple, offline ways like M-of-N that could work better in some cases.
I still am really keen to know what's going on with custom script/contract stuff and if it's going to actually happen at some point. Maybe my idea is no good but theres got to be other good uses for them.
I just wanted to make the point that if you are holding $5 million, you want a solution that leads to 100% chance of recovery. The M-of-N solution is exactly that. Do it once. Ever. No shenanigans. No maintenance. No chance of failure. But what you are proposing leaves room for things to go wrong. No matter how diligent you are, it's going to get annoying to do anything with your funds, even once a year, if you have to revisit safe-deposit boxes, redistribute transactions to your will, or whatever. You'll take shortcuts, you'll be in a hurry and say you'll deal with it tomorrow. For periods of time, only 0/5, or maybe 3/5 of your money will actually be recoverable if something bad were to happen to you. In a way, it kind of defeats the purpose.
I appreciate you are keeping an open mind. As you can tell, I've spent a lot of time thinking about these things
And I've also spent a lot of time dealing with users who didn't bother to even make a single-sheet backup and then lost all their coins when they forgot their passphrase. And people who chose to backup their Bitcoin-Qt wallet and then didn't realize they had to re-backup, or were too lazy to do so. And they can't backup securely, because they have to do it often. That's why deterministic wallets are so valuable -- anything that requires regular maintenance is going to fail. Even if you think you can do it yourself, and that you'll do it right--others won't. And even you, in all your diligence to do it right, may screw that up because you're in a hurry and don't have time to stop by the bank today to replace the inheritance transaction in your safe deposit box. Etc. But one thing is for sure: you make paper backups, you secure them hardc0re, once. And you never have to worry about it again.
Okay. I've beaten this dead horse enough. You get my point
I'm happy to walk through thought experiments with you about this, but I'm doubtful anything is going to beat the combined convenience and security of a 2-of-3, 2-of-4, 3-of-4 or 3-of-5 backup.