Shaun Shaun,I am a "specialist" and currently a business owner of a design and drafting company in CT. 

Hey @Keagan Scott, so I don't have any insight into Gary, IN but here is a blurb -"Those looking to rent out their properties for less than 30 days (about 4 and a half weeks) will have to get a permit, pay a one-time $150 fee, and have a city business license.

Now I'm banned for spamming and while I'd like to handle this privately I'm blocked from the messaging system. 

Your question has been debated between BP tax experts both privately and publicly, for example here: https://www.biggerpockets.com/forums/51/topics/819991-expens...And we ended up where we started: no consensus and no clarity.There have also been court decisions that support my interpretation, even though I personally find these court decisions debatable.

You have a job that keeps you busy, but you want to start creating wealth through Real Estate.  

Another thing, the threads move down the forums rather quickly because it's so busy, so the odds of your post being seen for long by very many people is minimal. 

I was told by a friend that his dad who runs an appliance business has "keys to every type of washer/dryer coin box".

Redlining IMO would only be an issue if @Jimmy O'Connor said to stay away or refuse to do business somewhere; he did not do that, he just pointed out property characteristics.

Cost of doing business.

Some investors also use a business line of credit backed by their cash flow, which can help with future deals.If you’re planning to scale, maybe start stacking that cash for the next property or even park some in T-bills for short-term returns.