This depends very much on your situation and personal beliefs. Even though crossdressing is not illegal in Canada, it may cut straight across the sexual values of your family and friends. On the other hand, it’s perhaps one of the least harmful or exploitative of all sexual unconventionalities.
Serious crossdressing can cost lots of time, energy and money. Whether you view it as a hobby or a lifestyle, make sure you budget for it. Respecting your family’s needs as well as your own goes a long way to maintaining trust, understanding and acceptance. The Cornbury Society’s “Significant Others” group offers support and a place to talk for spouses of and those involved with crossdressers.
Coming to terms with your (or your spouse’s) crossdressing can be an intense emotional experience. That can be a profound source of strength for you.