Finding a new area to invest

[Nicholas Junker]

I currently own a 2bed/2bth condo in Avon, Colorado which is located directly across from an awesome world class ski resort known as Beaver Creek Resort (it is Vail Mountain's sister resort just a short 5 miles down i70 to the west). Acquired this condo with my father for $205K in September 2013 and am currently breaking even on my monthly expenses renting the apartment out to some friends in the area. Other condos in this complex are currently being listed for $230-260 depending on remodels and these same condos were listed from $140-180K in 2012. The rental market is VERY strong up here in the mountains as housing shortages are very high forcing seasonal and full-time employees to find housing down valley up to 40 miles away from Vail in which many jobs are located.

My dilemma is this. I can't decide whether to continue to try and invest a buy and hold strategy in this market as housing prices have risen and are continuing to rise so dramatically that 2-3bed/2bth condos are impossible to afford and cashflow. Foreclosures are also non existent as well as duplex/fourplex units.

The future of this valley are huge multimillion dollar vacation homes taking over neighbourhoods and continuing to push affordable housing down valley to the west, farther and farther from free bus routes and easy access to skiing and recreational activities. 

Do I need to find a new area to invest? Is this market becoming over saturated and unaffordable? Am I missing creative opportunities to finance? Am i not looking at all the possible angles? (i still have a primary home buyers power in finding a loan) If i need to look into a new market, how do I begin?

Thanks!