Hi Ross. I lived in Lakewood (The Carlyle, I think) as an intern over at the Cargill mine for a summer many years ago. Lakewood is a great place to be, and I hope it does remain desirable!
I'm of the opinion that the time to invest is NOW. Trying to time the market is a fool's game. Get your money to work for you as soon as you can, whether it be real estate or the stock market, etc. I might recommend caution if I was trying to house flip, but house hacking changes the game a little bit. You need a place to live regardless of your investment strategy---so why defer that potential?
Through successful house hacking of my own home several years ago (airbnb of our upstairs bedrooms, specifically), my wife and I were able to clear about $30k of principal pre-payments as we moved to a more yuppie-fied place. Our three years of house hacking was completed in good market conditions, but had the market struggled, we still would have been happy to have defrayed our housing costs against a multitude of guests.