Taxability/deductibility of amounts received/paid pursuant to an interim separation agreement in two scenarios provided by writer.
The taxability/deductibility of payments vary depending on the actual terms of the court order. The courts have considered the situation where the governing document (decree, order or judgement of a competent tribunal or a written agreement) provides that the payer must pay the tax payable on the allowance in addition to the allowance itself, and determined that the tax payable will be considered part of the allowance and will be deductible as well.
Third party payments may qualify provided that the provisions of described in subsections 60.1(2) and 56.1(2) of the Act are met.
There is the possibility of a deduction as a medical expense, of the tuition costs. This will be a question of fact, individual determination required. Insufficient info provided to make any more than general comments.