That's a huge decision to treat nonchalantly. I'd rather be penny poor and dollar rich, than penny rich and dollar poor. It's the biggest investment decision of his life to date, and what a terrible taste it would leave in his mouth to have to sell his first house and be upside down. If he's going to have a $3,500 mortgage/tax/insurance payment, why not rent a cooler $3,500/month apartment? Eliminate the risk of a short-term decline in real estate prices, and buy a house when he knows where he wants to live for awhile longer. That way he could have fun as well. Maybe I don't know the market well enough, lol, can you rent a cool place for $3,500 up there?
On the other hand I do admire Matt's idealism and belief that the easy solution to a spending spree is to just make so much money it doesn't matter. It's beautiful.