We do have our retirement accounts, brokerage accounts, HSA accounts, etc… and will continue to invest money into those respective accounts for retirement purposes.With above stated, I would appreciate if  anyone can give me an honest opinion on how to start my journey as in what would be the best operation plan/strategy given my current situation and assumed future plans before partaking.Thanks in advance for anyone replying and assisting in the matter.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

But it's what my thoughts are and determines how we will operate and spend our money.

In each market I operate in I have someone available for showings this person is usually my runner who is responsible for quality control and restocking inventory but I've also used a cleaner for this.

And always  remember to operate with integrity  Thanks Tim!

should allow you to save for your second deal fairly quickly.Full disclosure: I run a turnkey operation based out of Birmingham, AL—happy to point you in the right direction and answer any questions that come up!

So, 400k - 500k sounds like lots of money but if you wanna operate in the 300k+ entry point it get can swallowed up quick.One strategy I'd try is to be a buyer at the auctions, win a bid on a good house, close on it in cash (you should be a great deal under market value) and then get into a delayed purchase bridge loan product which will cash you out a certain percentage of the purchase and supply the rehab funds. 

I’m not only working on my case with these buyers and a DeKalb Pastor & Chaplain of DeKalb Sherriff Office on over 2.5M...but this now appears to be related to a HUGE Mortgage Fraud Criminal Ring here in Metro Atlanta with quite a few of confirmed fraudulent documents on many properties as more evidence shows up.Some of the names I have confirmed provided or created fraudulent bank statement, operating agreements and forged QCD docs to obtain mortgages illegally then allow them to foreclose.

Some don't require you to have a property management company because they operate like a hotel.

It's a game changer once you have a few employees and operate that many so everyone stays on the same page.