As usual your analysis and your language skills are faulty. Please pay attention to what I said, "The mold cost is the same to make one fin or a thousand". This is true unless there is some degradation of the mold before then. Which you do not mention.
As to your analysis. The mold is a sunk cost meaning it was already paid for and cannot be recovered, consequently your allocations have no cash flow effect for Bob. I am not sure when (if ever) you took a managerial accounting course but the contribution margin approach has been taught since at least the early 1980s. If Bob is able to sell the fins for more than his variable costs (production costs, packaging, shipping, etc.) then he will have cash to cover his fixed costs. The objective is to maximize the total contribution margin. This assumes the rest of his costs are fixed period costs that do not vary with the number of fins sold.
As far as developing an exclusive product that depends on the margins and volume. He would be better off selling 2 fins each with a $200 contribution margin than 1 fin with a $300 contribution margin. I am not sure of what the elasticity of demand is for scuba fins, but Force Fins start in price where most other fins end. I am sure Scubapro would sell a Tactical Jet Fin for $500 if they thought they could get it.