After digging around for old 300/Charger VIN break-downs and comparing my VIN database and the registry, I believe the VIN breaks down as follows. I had started this with the intention of discovering what portion identifies the transmission, but it does not seem there there is anyway to identify the transmission type by VIN alone.

[1] Country of Origin
2 = Canada
[2] Assembler
B = Dodge
[3] Vehicle type
3 = Passenger
[4] GVWR & Pass. Safety
L = Restraint System Advanced Multistage Front Air Bags Sales Code (CG3) With Side Air Bags
[5] Vehicle Line
J = Challenger
[6] Series
4 = SE
5 = R/T
7 = SRT8
[7] Body Style
4 = 2 Door Pillared Hardtop
[8] Engine
T = 5.7L HEMI
V = 3.5L 6-Cyl
W = 6.1L HEMI
[9] Check Digit
0-9 or X. This value is used in an algorithm to validate the VIN. See Wikipedia for details.
[10] Model Year
8 = 2008
9 = 2009
[11] Assembly Plant
H = Brampton Assembly
[12-17] Vehicle Build Sequence
These last 6 are your serial #

In summary, EVERY single Challenger will start with the VIN: 2B3LJ (This is confirmed in that the 53,000 VINs I looked up yesterday 100% of challengers started with those codes)