Well, the thing about it is, all five series will always be there so there's no rush. You'll go through them more quickly than you think too.
As for novels? I can't speak intelligently on the TOS novels not having read any, though I'm sure someone can point you in the right direction. There's more ST novels than I could ever get around to reading though. The DS9 relaunch novels are great and pick up right where DS9 left off though. Some of the TNG novels are pretty good too. Once you get through all five series, I'd definitely recommend the Destiny novels by David Mack.