I believe they are more common in typical vacation spots like Kissimmee, Orlando, etc. 

Check out other for-rent listings in the neighborhood and see if this is common for the market.

It's less common, but some people do it. 

My wife and I have a regular W2 job so any cashflow made would just stay in the properties bank account for repairs and maintenance.  

2) Can you "keep your day job" while you get started?

If you can do better, great, but you really have to understand your market, do an excellent job setting up and operating your property and you have to stand out from the crowd to earn those higher rates.

Pretty much like everyone else has mentioned, property management is a hard job.

They are in a bad spot because of poor management, this is very common in medium-sized multi-family, roughly 5-50 units.2.

As a former bike mechanic I know renting bikes for a profit is a full time job because of the repairs.

Specifically, there's job growth (Intel, Honda, Amazon, Nationwide, etc) and the population is growing (unlike Cleveland or Cincy).