Oh man I still a bit nervous about this one.
We just signed a house for $427000K. We are selling our house for around $340000K. We have about $150K equity in our current house.
I really hate the fact that our mortgage will be going from a balance of $190K to $292K (after lawyer, and realtor fees). Our current house just doesn't work for us. We bought it as a couple that never wanted kids and well now we have one kid and are going to be trying for another. The things we dislike our in house can not be fixed with renovations - tiny tiny bathroom, no backyard, tiny bedrooms, etc.
This new house is perfect for us at 1500sq ft with a finished basement and beautiful backyard and absolutely nothing needs to be done to it for years whereas our current house the roof would need to be replaced at $10K and the kitchen cupboards and counters are in pretty rough shape at $15K.
We are still doing well in all other areas but man it makes my stomach flop a little bit.