Please don't take offense, but I recommend against this. Those videos might be heart wrenching to watch after a while. Perhaps it would be better to sing with the child now, and take a video of that. Then the child has a memory of his/her father to look back on, rather than an expectation to watch a video every year.
Here's why I say this: Dispensing advice via video makes sense, because the child may not be ready to hear certain things. But who are the videos for? The living or the deceased? At some point, children need to move on. Holidays should be happy events surrounded by living people, looking forward to the future. I don't think I would want a reminder like this every year. Imagine seeing the same person, at the same age, with the same voice, singing the same birthday song every year. It would be a reminder of loss, of the unfairness of life and the detriments of aging. (Sorry if that got too philosphical.)