Enjoyment wise for me these options really group into two tiers:
- Contender Tier: Options 1-2 are where the team is a contender, even when they don't win the cup. Cheering for wins is fun because you can see them adding up to a cup.
- Fodder Tier: Options 3-5 are where the team has no realistic chance of winning the cup barring a miracle run, so it is hard to care about wins or loses which are going to add up to nothing. Enjoyment in this tier has to come other things like individual player performance and team building.