[mr48chev]

These days there is no "most sought after year." It's about finding the AD truck that is in the best condition that your purchase budget allows for. Then it comes down to standard 3 window cab or Deluxe 5 window cab, then single piece door glass or doors with vent windows and then the 47/53 vs the 54/55 first series.

I'd say that 80% of the guys could care less what engine a project truck has, had or if it even has an engine. Good running 216's or 235's in a truck that you plan on putting a V8 in are just something that you need to figure out how much to sell for and usually the truck's seller thinks that they add a premium to the price of the truck.

For a guy contemplating keeping a stock engine the 216 is ok but with babbitt rods and dippers on the rods rather than pressure oiling to the rods they aren't the best idea for long hard road trips. If you can do gentle road trips they work fine. The guys who want to get out and drive on the big roads should look at 235's though.
We all have different ideas on what driving our trucks entails. Some will never get further than the local cruise nights while others will load up and head out across the country several thousand miles as soon as the truck is on the road and squared away.

As for liking a particular year or model. Personally I like the 47/50 trucks with the one piece windows and the vent on the driver's side of the cowl. I know several other guys who want the 52/53 trucks because they don't have the side vent that they think clutters up the lines of the truck. I learned to drive in a 54 Deluxe cab truck with every bell and whistle that came on 54 trucks on it. Still I don't get excited over the curved windshield or the bulky to me grill.

Basically it sounds like the OP is asking what year truck will bring the most money after it is finished rather than what one's personal tastes in trucks are. As everyone else showed we tend to love the ones we have just because they are the ones we have.