Hoskins is a model professional: hardworking, robust, always willing to fill in anywhere to do a job for the team. His character is absolutely unimpeachable and he should be applauded and appreciated by our fanbase.
However, like a lot of 'utility players', the constant switching of position has probably been to the detriment of his development as a footballer. Ben Tozer was a similar victim of the 'utility curse' when he was here and Johnson tried to turn him into a defensive midfielder; in recent years, Michael Duff has allowed him a sustained period of development in his natural position of centre back at Cheltenham and he has now blossomed into a title-winning captain who has just moved clubs for a substantial six-figure fee.
I think the constant switching around has contributed to Hoskins' main weakness: his 'footballing brain' and lack of 'positional sense' - too often he shoots when he should pass, dallies on the ball too long, dribbles up a blind alley or chooses to pass to the wrong teammate.
If we continue to play him as a first choice winger in a 4-4-2 I would be concerned about our overall creativity. His crossing simply isn't good enough to play on the wing in a 4-4-2 IMO, and he doesn't get enough assists. He was brought to the club as a striker and he should return to this position IMO, particularly as Brady called him the most 'natural finisher at the club' (ahead of Rose and BAS) last season. As others have said, he's also good as one of the three behind the striker in a 4-2-3-1, where his capacity to carry the ball at pace can cause problems.
Ultimately, he's been a great servant and I'm glad he's in our squad. It's certainly not his fault that he's been played out of position so much. Managers love him due to his workrate, pressing ability and physical fitness: it's no surprise that they've constantly found a way to shoehorn him in somewhere, but this has often been at the expense of our overall tactical coherence - hence the 'Hoskins dilemma'. However, if Brady is serious about producing 'bums off seat' football and developing us into a team ultimately capable of sustaining league one status then he needs to resolve the 'Hoskins dilemma' once and for all.
Great post Bungle