There are so many options to choose from, that I think narrowing it down based on your son's own interests is a good idea. Along the lines of what Bill suggested, I think I would want to find him something that he can feel a personal connection with.
Does he have a favourite current team that has pre-war roots?
Are there any particular pre-war players that he knows of and is intrigued by?
If you can't narrow his focus down based on his current interests, then perhaps you can challenge him to do a bit more research by handing him a stack of books within your own realm of expertise/interest, and offer to supplement his investment a certain amount for each book he reads. Maybe that turns this into too much of a crusade, but I think having him educate himself about what he's about to invest in has a lot of upside.
Just a thought.
Regards,
Richard.
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