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MarkMike nailed it... those are some great basics of pennant collecting. Go after what you like, whether it is the artistry, a favorite mascot or logo from days gone by, or a pennant that commemorates something special to you (World Series, All Star Game, Championship Season, etc.) These dated or year-specific pennants tend to be more expensive, and are always more in demand.
The "holy grails" of pennant collecting are the Jumbo Oversized beauties from the teens (and earlier). These pennants measure 34" to 40" long (not counting the tassels). Mike and I tend to salivate all over these, as do many other collectors. They are rare, and command a big premium. I'll attach a couple of photos, just to give you an idea...
Lastly, beware of reproductions. There are many repros out there. Many were made not so much to deceive people, as just to copy the beautiful graphics (and make them available to the public at an affordable price). Mitchell and Ness manufactures most of them, and some are so close to the originals, it's tough to tell them apart. The telling factor is that most of the repros have raised velvet type graphics, instead of painted (screened) graphics. If you see puckering and some crazing/cracking, that's actually a good sign.
Shown for size difference comparison... the Vander Meer Pennant is full sized! Hope this helps...