I'mI'm doing the Alphabet challenge on FMC and I have removed leagues so there is only 3... The top bit is exactly what I try to do.Theoretically, you should be able to save (while playing Football Manager Classic) to the cloud; 2) exit the game (entirely) wait for Steam to upload; them go to VITA, then download the file.
BUT I still get the "CANNOT CONNECT TO STEAM" errors with certain files, randomly, so I save the same exact save (say I'm playing as Arsenal) and save it under 'Arsenal1' and 'Arsenal2' etc etc - I usually save around 5+ files just so the cloud gets to sync at least one.
Yeah I dunno why it does that, but it does. Dunno the fix.