If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

From what you've showed, I'd say your main focus should be working on your personal finance foundation rather than diving into an investment.

I recommend networking with other investors and asking for personal recommendations, using companies (not individuals) with strong reviews on Google, etc.

Personally, I like "light" value-add and "core plus" investments that are larger buildings.

I have personally invested in over 30 individual deals.

If I were the money person, I would want to see the deal first.

My loan person said we might be able to do a escrow withholding where they keep the money for repairs until after closing. 

I don't live in IL, and I'm by no means an attorney, but let me say this - when you wholesale, you're selling an assignment of the contract, which is personal property.

When people make a lot, they also tend to risk a lot.for the average person, 1 home every year for 10 years is a doable and strategy that can get you there - slow and steady but faster than the average person. 

We have an estimator tool where you can view various appreciation and settlement scenarios so that you can see the numbers for yourself without providing any personal information upfront.