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I would encourage staying around 218° or smaller. a 218° will still have a noticeable idle, but a lot less "snowball" effect of changes that you need to do to make that cam work.
If you're looking at buying aftermarket heads, look for 305-specific heads. The combustion chambers are very small so that you can have good compression. 60cc or less, likely. I think Edelbrock among others have a 58cc head. Once you pick your combustion chamber size, then see what intake volume they offer in that size. Smaller volumes keep the port velocity high which benefits torque - desireable on the street, and in a truck.
An air-gap intake will be a bit more of a challenge in winter, as there is no heat to help vapourize fuel from the TBI or carb. It will likely run poorly and burn more fuel until it's fully warmed up. You ~can~ put TBI on an air gap (they sell TBI-to-carb-intake adapters).
What do you think about the fitech unit? Looks pretty cool.