Hey everyone, great discussion and points of view. It's certainly interesting see the variety of perspectives on this issue, and as @Austin Fruechting mentioned there are so many different ways that it (RE) can be done.
When I originally asked the question, I was mulling over the 4 forms of wealth that RE provides (cash flow, paying down the mortgage, tax write off, and depreciation) as mentioned by @Brando Turner and @Josh Dorkin. I had figured that the initial investment and cash on cash returns could be comparable, but the tax incentives and depreciation would favor one market over another and thus favor one strategy or another. I understand this could be understood much more comprehensively by running the numbers of prospective properties to find out.
Additionally, the thought with Jacksonville (or Tampa for that matter) vs. Denver is that the Florida markets still have sizable appreciate projections to benefit from. So not only was the thought to invest in a cheaper market, but also to capitalize on the upswing of those markets. Thus getting a little extra juice from the out of state play.
