Yeah some are harder than others, depends on how much time you want to put into it, I'll give you a little breakdown,
The Debutant
As easy as they come, just need to play a competative game
League Champions
Depends on how quickly you can get to a decent team, but it is possible to get after 1 season if you are lucky.
League Best Eleven
Just need to be in the team of the season, can be done after one season.
Champions League Debut
Will take until at least the second season as it's highly unlikely you will get signed by a CL in your 1st season.
Super Star
3rd season at the earliest as you need to play in CL, progress to the QF's at least & be the best player in the tournament which can be difficult.
Pride of a Nation
You need to play at the World Cup Finals, so the end of the 2nd season at the earliest & if you miss that then end of the 6th season. To have the best chance of getting into the NT early its best to set your nationality to a country that has a NT IG, but has a small pool of players.
World Footballer of the Year
In previous years the only time I have ever got near this one is when my team has done well in the CL or WC. Again being the best in one or the other will give you a good chance.
Proud Skipper
You need to stick around at a club for a while although I have been made captain after 1 full season at a club before.
Mr. Versatillity
You need to buy the option from the shop to learn a new position, I think it's around 500GP, then it takes about half a season
The Multi Talented
Same as above but you need to buy the option to learn a new skill
If you don't enjoy the mode but want the trophies I suggest dropping the skill level right down to make things easier.