Sure beats lurking in the shadows :) Personally I would look to maintain ownership as long as possible (unless I were, say . . . fleeing the state), but I would want to do that while maximizing overall investment ability. 

What are some good things to study/learn before diving into the real estate world.

Real estate caught my attention my last semester in university so I included as much of it with my studies as feasible.Fast forward...I'm on the brink of getting a property under contract.

Is the city responsible for maintaining it or what permits would I need to level/gravel it?

And every Agent should be open-minded and study wholesaling instead of bashing it. 

@Justin Megna this may sound broad, but study every factor/variable that may have an effect on your investment strategy and specific target market.

@Douglas Spence I am near closing on a cash out refi that will actually lower my payment (slightly) and provide a good base of cash for down payment to purchase those properties while also maintaining adequate reserves. 

But again, its quiet, and well maintained street.

What are some of the other reasons for maintaining regular annual rent increases?

They consider them disposable rather than fixing/maintaining them most of the time.