If you haven't already, read "The House Hacking Strategy" by Craig Curelop and "Long-Distance Real Estate Investing" by David Greene.

West Oakland is plenty popular with working professionals where school isn't as important as commute/social (food, nightlife, stuff to do). 

I'm planning to invest long-distance and want to hire a contractor to check out the property to see if this is a feasible option. 

I we own a large updated one bedroom condo free & clear in Burlington,NJ The areas is great major retail with in walking distance.

I had been kicking around doing something up in OKC, but the distance has me spooked.  

what would it take for you to travel to the market, are you willing to commute?

I just read and took comprehensive notes from three books on real estate investing:- Long-Distance Real Estate Investing (David Greene)- The Book On Rental Property Investing (Brandon Turner)- Home Owning For Dummies (Eric Tyson & Ray Brown)I was particularly drawn to Brandon Turner's REI business plan templates for new investors, and I liked his ten-year fourplex trade up model.

Having worked in the Healthcare field in Massachusetts for more than 23 years and having lived on the South Shore, I can tell you how much of a hassle it is to drive or commute via public transit into all of these top academic centers in Boston.

My question is for investors currently investing in Milwaukee or any long distance investors.

No one will want to commute an hour to school and no family will rent a short term rental over an hour away from Disney.