You are going to face (at least) two problems in this scenario:
1) The expenses you mentioned (new roof, gutters, remodeling) are improvements, rather than repairs, and, as such, you have to add them to your basis in the home (and you should be keeping track of your basis) rather than deducting them immediately.
2) Since you would be "renting" the home at, what appears to be, below fair rental value, you would have to report rental income on your income tax return but your expenses would be limited to the amount of income you reported (i.e., the income and expenses would be a wash, leaving you without being able to claim a loss).
You might want to consider consulting with a tax/legal professional in this matter for advice regarding estate planning with respect to this home and any other property, as well as maximizing the total return from the current situation.
