Cold Storage failsafe

If I were to hold bitcoin in cold storage for someone, but was worried about what happens if something happens to me, what can I do?

My thoughts so far are:

1. Make a 2-of-3 multisig wallet. I hold all three, give one to the owner of the coins, one to a trusted third party who is instructed to only give them the second key if they have verified I am dead or something like this

2. Is there a way to create a programmed spend that happens once a year, on a schedule, that I can sweep back into the old wallet. Give the owner the free and open keys to the dump wallet, I just keep sweeping it back into the main hardware wallet each year? This way, if I am not there to access the funds, the person will eventually get the funds dumped into their account and I will not be there to sweep it back out. Is this possible?