Obviously there is more management on my part and more wear and tear, but is this a smart move?

Be smart and protect yourself, screen your tenants thoroughly and provide a quality product and I doubt you will need an attorney anytime soon.

Everything I've read suggests that the technology infrastructure associated with the big guys is the best way to maximize pushing rents and occupancy: dynamic pricing, web penetration, etc.  

If I do decide to go that route, would it be smart to rent for 3 more years in Charleston?

Some people think that technology will make real estate agents obsolete in the next decade.

In any market, it would be smart to track and contact sellers of expired listings.

If smart enough to plan and buy investments probably smart enough to plan for taxes.

But there's nothing like getting some business smarts from people that have been there.  

Technology and social changes are the most determining factors for respondents. 91% believe that technology will change the way we use real estate assets.Cars without driver and incremental use of car sharing, will free the space in the cities, with less space necessary for car parks.The Internet will definitely modify the real estate business, both in retail and residential.The 3-D printers will provoke that it will not be necessary to store products, nor even to move them, since they can be generated at the desired time and place.The analysis of data allows a better understanding of the behavior of potential customers, as well as measuring the experience in the process and the satisfaction of those who are already customers.

"You learn best from hard mistakes"  Smart investors know the road to success is to learn through other peoples mistakes.