Nope, now is a better time than the previous two expansions to get into the game... The two new races means a lot of people will be making a lot of new characters, so plenty of people in starting areas to level with when cata launches...
Plus all of the old races and starting areas are being updated (such as Humans getting Hunters and Tauren getting Paladins, etc) and the starting areas are being redone to make them both more enjoyable and more efficient to quest in...
As for the old content, yes it will be dead for you unless your guild runs old content as the gear and drops there apart from mounts will be completely useless to an 80... Depending on what class you play though, you might be able to solo some of that old content... You may even be able to solo some of the old 20/40m raids if you are a DK/Pally with a lot of dps/self healing... And what you mentioned about gearscore, it doesn't take long at all to get geared now... 4.0.1 redid everything... You can just skip Tier9 armor altogether and purchase T10 and justice points which is the new currency are very easy and fast to get, some random heroics can give you as much as 140 from one run that takes 20-30 minutes...
And to anwer your question about what you need to buy, yes you need to buy the vanilla game and all of the expansions... Look for sales, when I first got into this game I got the battlechest that came with the vanilla game and BC for $20, plus 30 days of game time... Then once I got up into the ~60's I bought Lich King for $20 in a sale on Amazon (and this was only about 6 months ago, not back when WotLK released)... So just keep your eyes peeled...
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