I am not a tax professional but it is unlikely one can meet the rules to get the free 2 weeks of rental using a timeshare. I do include any rentals I do in taxes but usually have enough expenses to wipe out most of the gains. I think few people besides me even include it in their taxes. I know when I first mentioned it to my tax guy, he said no to even worry about it. But I insisted though if it'd been a one time deal I would have just let it slide.