Cha Ching! That's a nice amount. If I had $1000 to spend I'd get two used bikes!

A used Volpe runs ~ $5 or 600. Great for 80% of your commuting time.
An old used 12 speed runs $50 -100. Use this one as a backup or on heavily salted roads.

OOOPS. These are US dollars not CDN. You're still under 1000 CDN with this approach.