Is it possible to put a Tiger sail up in a xwind?

I put my Tiger in a place where there is no room to move it into wind to raise the sail. Whenever the wind blows in certain directions at the beach, it is close to impossible to hook in the sail. Any tips on how to beat this dilemma?

I also just noticed that the sail as it came when new was rolled up in a way that makes it difficult to put up and take down. I have switched directions of the roll although with great difficulty. It seems to be more hoister friendly now. Any comments?