Chicago - New Investor - How to Find First Deal

[James B.]

Hello,

I am a new investor/ will be soon.

I am 20 years old right now, with about 1.5 years left in school.  I already have plans to take a job paying about 55-65k a year.  First, I will max out the 401k as the employer match is 100% that'll leave me with about 20k to save the first year.  Raises are likely to be significant and hit 100k+ by the time I am 26-27 or so. Assuming a 6% annual return on maximum 401k contributions + matching, I will be done saving for retirement by the time I am 31 or 32, which will free up another 15k-20k for investing. 

This leaves me with the possibility to save up at least $20-30k annually.

I believe it is more than do able to save that much or maybe even more, by the time I hit 100k I plan to save almost half if I can.  

That brings me to the first question

1) What should I do with the money while I save up? Should I invest it in stocks, mutual funds, etc. (it seems like over the course of saving up even 5 years this makes sense, but there is also the risk I could loose it all and end up with no money to invest in the real estate)

2) How much cash will it take to get started with a really solid property in Chicago, IL?

3) What are the required financials for a mortgage? Credit score, tax returns? What is everything I will need to get a loan? 

4) My first property will likely be my first home, where I live in 1 unit and rent the other unit(s), is this a good option?

5) Is it realistic to attempt to cash flow 20k/ month by the time I am 35?

6) I am mainly investing for cash flow, but appreciation wouldn't be bad either.  I am going into construction management and am familiar with renovations.  What renovations are likely to add additional value to the rent cash flow? Trim work? Wood flooring? etc.

7) Where should I look for my first property?

8) How often will I be able to purchase additional investment properties?

9) I prefer to avoid low income neighborhoods like I see a lot of investors flock to, is there a reason for this?