For fear of stating the obvious, much of the value of a classic bike (new or vintage) is in the eye (or soul) of the bike aficionado. A Bike must trigger in you some kind of musical resonance. A particular kind of lug must resonate with you, must unleash beautiful memories, must wrap around your soul and make you a wide eyed youth again. The bike that attracts you says a lot about your bikeducation and knowledge of bichystory. You can't fault a young man for loving an up to the minute aluminum road model because his exposure may only allow him to make distinctions based on what he has seen. A Cannondale with super smooth welds makes a rippled welded bike look crude. A cotterless crank makes a bike with a cottered version look like the recipient of hammered aggression ( I know this one will raise flames from lovers of pounded history).
Then there is the element of sweat equity. A bike that you have sweat away your life on, will always have a special place in your life. Here the spirit of the rider imbues the steel with a soul if didn't have before. For this reason, I will always have a warm affection for Sturmey Archer three speed transmissions.
There is the special history that a particular bike has with you. Where and who were you in space and time when you first saw a Paramount? Owning a Paramount may bring you closer to being that man (or woman) again.
Masi or Waterford? I'd have to go Masi, which for me has history, beauty and mystique. Waterford is crystal, isn't it?
By the way, I believe that Sheldon Brown has earned the right to own a Raleigh mountain bike. Ugly as they may be, they are fun, if you don't mind becoming a paraplegic when you slam into a tree or fall off a twenty foot hill. I sometimes fell three times an hour, before I sold mine. These things maybe real collectors items one day, as the majority of them self distruct from impact and become bike store dumpster decorations in a few years.
Garth, still not as fast as the fastest peloton monsters around here, but not giving up on my 531c Raleigh, Libre.