or would you stick to better more desirable areas like Seminole Heights where you get more high end tenants.

It's a very desirable area. 

Here's a link you may find useful. http://www.foxbusiness.com/personal-finance/2013/08/07/tax-rules-on-renting-your-vacation-home/A word to the wise, however, vacation rentals or "Air B&B's", the new trendy cliche of the day, are not always the most desirable investment for the unseasoned investor.

The house itself, though once clearly desirable and prestigious, is completely dilapidated.

I am a young and motivated entrepreneur with great desire to learn more about this vast world of real estate investing With a main focus in multi family and commercial real estate.

I want to learn more about real estate investing so that I can have the knowledge to act on my desire to make it my career.

On the bright side, I was able to clean out then than desired tenants and boost rent from $2300 to $2600 and have room to increase to $2700-$2800. 

Then you can determine what it takes to find your desired properties.

Depending on their lease agreements and your desire to keep them as tenants, something to consider.  

Or is it only based on your desire to not have your "life interrupted" by your customers?