Not any easy answers to this one (and I have spent WAY too much time looking into it).
First of all, pick a tires. As someone mentioned, everybody has a (different) favorite. Now throw out all of the tires you want since you won't be able to get the license to make them.
Second, since most of all the molds are long gone, it is $5,000 to get a single mold made.
Third, since you can't license a design, you will get to design your own and nobody will like it since it isn't truly "vintage".
Fourth, Panaracer has the molds for the Timbuk II, Smoke and Dart. We did the Timbuk II tires and have sold about 150 of them in 2.5 years at $29 each.
Fifth, rubber and transportation cost have skyrocketed. We came very close to doing Smokes but they would have had to sell for $40 each. The black wall versions are still available for $15 on sale in the US.
Sixth, you have to do 300 tires which is a pretty big chunk of cash and as I mentioned we have sold half of our tires in 2.5 years.
It is a project that sounds good on paper until you try to get it done.
If anyone is truly serious about this, give me a shout.