I never really chased any custom sets like you describe, although I would try to get all of the subset cards, like the 75T MVPs or the 76 Topps All Time Greats, etc.
I have played outside the box a little more with autographs, such as trying to get as many Dodgers, those who played on an all star team and the item doesn't have to match the year or team.
To address your example, if I were to assemble a 1955 Dodgers team collection, I would go with the 56 Topps set for a couple reasons. First, I like the design better. Second they show the 55 stats and these guys were actually on the team in 55. With themed sets like that, it is possible that a set made in 55 for example may have a player who moved on and never played with the 55 team. Lastly, although neither year is complete for the team, I believe the 56 set is larger than the 55 with more players to collect.
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