If I was to go this route today, I would probably not wear the watch but keep it pristine for all those years in a safety deposit box. I think it would be very unusual and cool to hand my daughter a brand new watch from her birth year and let her be the first wearer. It also allows me to buy a smaller ladies model - which I would not want to wear for two decades.
The other reason I would go this route is that - like most watch lovers - I will likely not wear a single watch so extensively or for so long that my child would strongly associate it with me. Not in the way at least I associate my father's 1966 Omega with him as he wore it for 30 years straight until he went to a quartz Movado.