Judge Posner's criticism of Heller
At The New Republic.
Generally, he's a good thinker and writer. But not on this subject.
UPDATE: Federal laws relating to guns were pretty sparse until 1968, so indeed there was little reason for the Court to take a 2A case. If I recall correctly, around 1902 there was a law banning pistols from the Postal Service mails. Then the 1934 NFA, applicable only to full auto, short barrels, and a few other things, and still allowing those if registered and taxed. A 1938 National Firearms Act, which didn't do much -- provided for licensing dealers (I don't recall who had to get one) and they had to keep simple records of purchaser's name and address. A few prohibited person categories, chief one being convicted violent felons. Hard to see much of a 2A test case there!
Also, Prof. Wm van Alstyne has pointed out that the first case in which the Court struck down a Federal law for violation of right to speech and press... was in 1965! What we regard as normal judicial function, a careful review of laws for constitutionality, people bringing test cases, the cases getting to the Supremes, is very much a function of the last 30-40 years. That the Court didn't recognize a right as important until recently represents quite a common situation.