As the old saying goes, "it is better to be an idiot on an uptrend than a genius on a downtrend". One of the reasons I chose to start investing 450 miles away from where I was living was the trends. Jobs were being created and homes were selling in the area I chose. The city was right in the path of development, homes were priced right and I felt like there was a definate uptrend coming. The city I was living in at the time was still moving in a downtrend. There is no sense in investing in an area still moving down because the best deals are still to come. Although it maybe easier to start investing in the town you live in, once you get some experience it may be a good idea to start researching other areas.
You've got to find your obstacles and call them out! Unsheath the sword, and do battle with whatever it is that holds you back!