Hi Sy,
Whilst I don't work with York specifically I can perhaps help with some of the points raised in your post.
1) I'd have to look at whether injuries are covered the same way as transfers within the game - especially when choosing the 'Real World' option.
2) As this is the Early Access some data is yet to be in its final form. Now this loan deal has indeed been cancelled and Whitley playing regular for the side - I could imagine this has already been tweaked behind the scenes
3) This is something which is an FA ruling and therefore cannot be circumvented. For month long loans they simply cannot be cancelled due to this ruling.