There's no way of getting around the fact that this character has a ton of essentials that need to be included. This should definitely be beefier than the usual set but I don't think that splitting it in two sets is necessary; as far as the outfit goes its only a different jacket and shirt.
If everything gets included, upping the price to cover the extras would definitely be part of the equation. I'm sure there are a few focused, sensible ways (not a la Vince mayhem) to offer everything. Two ways that come to mind are: a beefed up reg set/DX offering at a higher than usual price. Reg set could be Mohawk sculpt with matching outfit, sculpted belt buckle, shades, knife, all 4 guns, arm "gun slinger" and the rig. DX could be long haired sculpt, plaid shirt, bomber jacket.
Or another method could be offering a regular set as I listed above and then doing an expansion pack type set (instead of a DX) that includes the long haired sculpt, plaid shirt, bomber, clip board & cigar box.
I'm sure that people (myself included) would want to have a shirtless 'talking to me" version but hat doesn't seem possible because the lack of the right body. The BL is one of the only options and I know people use it for Rick but IMO the skin tone is way too Asian to be suitable for a Caucasian character.
I do think that Bickle calls for a Slim TTM22, maybe on long foot pegs or maybe the boots alone could boost him to the proper height. Either way he should be shorter and skinnier than the average (TTM18) figure.