So what you're saying is: if the observer on the 2 lightyear long spaceship says that the distance between the earth and the star is 1 lightyear then the front of his spaceship is behind the star. However to an observer on earth the distance to the star is 22 lightyears and the length of the spaceship is contracted to say 0.1 lightyears then the front of the spaceship is in front of the star.
So the question is, does the spaceship fit between the earth and the star or not? This is equivalent to the
ladder paradox where instead of asking whether a moving ladder fits in a garage you're asking whether a moving spaceship fits between the earth and the star.