My brother bought a house in metro Detroit in 2004 for around $90k, a little under appraised value. It's current value is around $50k. In 2010 we agreed to try to rent it. However, the process to fix everything was slow while we lived there, so we moved out, thinking that would give us ample time to work on it without our stuff there. This wasn't really the case as neither of us showed urgency to finish fixing it up. It is also located in a lower income area, and much of what we did to the house was overkill. We ended up finally getting it advertised in the summer of 2013, and rented in October 2013, slightly rushing to get a tenant in when it was finally ready.
Lessons learned
1) research everything quickly, read blogs/forums to get more info and learn
2) scout the area to see what other houses in the area look like and rent for
3) move out and make a plan to fix things accordingly, and then execute the plan as quickly as you can
What was a loss leader for my brother also turned into a loss leader for me and an even bigger loss leader for him since we wasted a couple of years goofing around.
We are both marrying this year, but are considering future rental properties in the near future. We will do the second one the right way!