Chicago is an awesome city but as @Crystal Smith mentioned, it has 77 neighborhoods and each one is a bit unique so you'll definitely want to do your homework.

Don't focus on anything like branding, super fancy systems or fancy CRM's yet - most of that kind of stuff is just shiny object syndrome.If you have the budget, I'd look into hiring someone to handle the lead generation & appointment setting process for you, so you can focus all of your efforts just on showing up to apps, negotiating and closing deals (which is the most important thing in your business, the lifeblood of it).If you don't, you'll have to do that yourself until you start working on some deals and start bringing some cash in.The most important thing is that you focus on what actually matters and ignore all the noise in the market - just do what needs to be done, and ignore everything else.Hope this helps?

This is a concern with several of the electronic payment services..... they don't allow you to block someone or block partial payments etc.I don't use pay pal for rent, but i'm interested to see if you find a solution, since its not unique to PP alone

Shiny objects can derail a new (and frankly seasoned) investor.

On one hand, it would save money to replace it, I’m keeping a rare piece of history, and I’m creating a fairly unique kitchen.

@Ricky Cassidy - I'm not aware that Anne Arundel has unique requirements within MD Code. 

For starters, you'd want to consider the location and general age and price of properties in the neighborhood, ratings of nearby schools, amount of crime, vacancy (homeownership and rental), plus grocery stores and shopping centers nearby.A lot of this info can be found online (e.g. school ratings, crime maps, property age, grocery stores and shopping centers), while some of it can be determined by driving the neighborhood and talking to folks that live in the neighborhood.Asking police about a neighborhood might give you some objective info on crime, talking to property managers might give you info on vacancy and rent prices, and talking to a real estate agent might give you info on property age and price. 

I realize it's smarter to have my money working for me, even while I'm asleep, than it is to trade my time for money.If I am going to trade my time for money, and I DO that too, the main objective, aside from helping others and filling needs, is to bring in more money so that I can put it to work too!

There are unique requirements for different concepts from mechanical systems, to handle the kitchen equipment, hoods, water heaters etc.

Each neighborhood has its own unique features, pros and cons and whether something is a "pro" or "con" is more subjective than objective depending on each investor.