One step down...
Matt and I began the process of seeing prospective homes on May 8th of this year, and — after having viewed nine properties — have found a place which we agree might be the best fit for our current and future needs.
In terms of location, this property is close enough to a major road that it's easily accessible by car and the York Region Transit bus service, which goes in to Finch station. Honestly, this was the biggest problem I had with the idea of moving North of Steeles — my jobs tend to rely on my ability to get to the TTC. Our real-estate agent assured Matt and me that what we'd get considerably more house for our money if we looked for townhouses just North of the city, rather than trying to stay on the subway line. So we'd have a place we could grow into, not something we'd have to sell in another 2-3 years to look for something larger.
As of yesterday, we've submitted an offer which has been accepted. We've yet to have the home inspector review the property, and a lawyer still has to go over the documentation. One concern I have is that the reserve fund is apparently diminished due to the fact that the units needed new roofing in 2006. We'd been told that the condo board decided on having each unit pay $1000 per year over 5 years for the purpose of not depleting the reserve fund, so I'm curious to see what comes up in the documentation.
Otherwise, I'm excited enough about it that I've already started considering what I'd like to do to make the place a home. What I like most about it is that it's aesthetically already in "move-in condition", for my tastes. Any renovations, tidying up or re-painting would just be icing on the cake.