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identify7In my opinion, personal preference plays a huge part in the selection among the sets which you mentioned. For example:
Goudeys are most similar to the more modern cards, and match those typical of the '50s well.
To a somewhat lesser extent the Diamond Stars are also similar, but incorporate the art deco design features common for the period of issuance.
A type set of Orioles is a good choice from the standpoints of flexibility and the ability to demonstrate the changes in the history of card production.
The t206s are quite popular, and like most of the above, readilly available.
The other three, to me, are an acquired taste.
One can become lost in Old Judges. Many never recover. By contrast: the monster has many survivors, although none are unscathed.
Ruth strip cards is a place I am often tempted to go, but the hole is deeper than many think.
Cuban cards are numerous and varied. A specific focus should be developed prior to jumping in.
The above is intended to be the start of an analysis or discussion. Without any more input it is difficult to make a recommendation. Which has the best upside? Maybe the Ruths. Which has the most downside? I think all choices are strong.
Everything above is one person's opinion.