Way easier and cheaper.

Although, I have turned the property I am currently living in (I own) into a duplex which would allow me to rent and move out into another to have as primary residence. will this make things easier?

I'm ready to invest another $50k or so and was considering investing out of state, small multifamilies in less desirable areas near me, or to continue investing in my comfort area.About the target property: I would classify it as an A or A- area based on what a lot of people call B and C areas around Chicago.

@Nabil Suleiman  As this would be my first property, I feel that buying local would be easier for me to manage and learn from. 

Can you tell me for each above, give me a decent  number target, a good #,  and what is a great # to achieve on each item above.Also, for me,  I have two rentals,  1st bought in 2001,  2nd bought in 2014.What is a decent, good, and great $$ amount for cash flow to expect YOU would expect on a home purchased back in 2001, & 2014.  

You’ll want to spend 3-5k a month on marketing and you’ll want to figure out which type of list works best for you to target.

It's nice to send thousands of letter each month but if you are not targeting your audience, you are shooting blanks.

Raising money has never been easier since it is sitting on the sidelines looking to get in the game with a great property.

I know Eagle rock is the place to be, but also the other one also pays for itself.Eagle rock has a long way to cover its own expenses as the other 2 tenants pay so low rents and does not seem like they will be going anywhere any time soon, so I am not sure if I invest in the Eagle Rock property and carry a large negative for at least next 10 years or go with the Bread and Butter property and stay in a not so good neighborhood.What do you guys think, a better neighborhood or an easier investment in a not so good area?

Banks are easier to work with and they should cash flow instantly.