I'm a newbie still when it comes to real estate but if I was looking to buy in an area other than where I lived it would probably be a rental friendly condo near a popular tourist destination. I would then look for a reputable property management company or I know some condo complexes even offer to help with renting your place out and cleaning up after guests leave. Come to think of it I stayed in a place like this on my honeymoon in the smoky mountains. I just walked into the office there and asked if they had anything available and they rented me the place place for $200 a night for a couple nights. It looked like a really nice private hotel from the road but turns out it was actually someones condo they were letting the place rent out. I bet they made a killing there.
Also I just thought of if you have family in other areas / states that you visit often you could look there or have them be on the look out for any good deals.