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From my own experience, Brazilian 3rd Division is hard, but the Turkish 3rd tier proves to be difficult as well.
German Regional Leagues could be considered hard, but that's mainly because only 1 team per division goes up.
Playing with Man Utd I've always found the German league quite impossible (I'll be here all week, be sure to tip your waitress and not to bring any firearms to my shows!)
Bu honestly, I've found my home leagues the hardest, it's difficult to play here having all these prior opinions on the players here and being quite controlled by them rather than the in-game players!
Originally posted by dirty1982dec:
i find manager of the month quite hard to win at the moment, you see no matter what my team does, someone always pips me to it.
Couldn't agree more, yet to win it after 3 and half seasons, even when I win 6 out of 6, somebody wins it ahead of me. Sure it'll come for me one day though. I patiently wait.
Getting out of the Conference North / South is easy I find, as you can loan as many players as you like. I just loaned a full team of young players from clubs much higher up the ladder on full-season deals, then romped to 113 points.
However when I got to the Conference National I tried to repeat this and found that I could only loan 5 players on season long loans, meaning my squad was woefully underequipped for playing in the next level up.
Frequently at this level you've got no money to buy players with either, so assembling a squad is almost impossible.
Most difficult competition to win? 
(I'll be here all week, be sure to tip your waitress and not to bring any firearms to my shows!)
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