And given #3 above, it leaves about 20% of rent for all other expenses like property tax, insurance and other PM expenses like leasing fee, eviction fee and other minor expenses like for e.g landscaping, pest control etc.

Property taxes are 2% instead of 1% for landlords as a general rule (some districts may  be slightly higher). 

@William TaylorMichigan has some of the most complicated property taxes in the USA.

To navigate the nuance in the laws properly for compliance and to accurately structure our LLC, I am looking to consult with an attorney who knows immigration + business + tax laws. 

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

be sure to stick to your 70% rule for the flip, know your numbers. run everything conservatively. overbudget for time and costs but 15-20% Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The buyer decides where they want professional help, and what steps they want to do themselves.Have you found anyone offering flat fee buyer brokerage/agency in your area?

We lived in the property for 2 years and rented for 2 years to tenants, so by selling now, we ensured that we could avoid capital gains taxes.

Selling the property within your Solo 401(k) and returning the proceeds to the account simplifies compliance and ensures tax-deferred growth (or tax-free in a Roth Solo 401(k.)).

It's a balance of cashflow and wealth accumulation.One of the goals is to have tenants pay as much of your cost-of-ownership as possible (loans, taxes, insurance, etc.)In high-cost areas, any Class A or B property you buy will usually negative cashflow for the first 3-5 years, until rents rise enough to cover the negative cashflow + rising taxes & insurance.Investing OOS increases your risks because you may not know the market and you can't check on everything/everyone all the time.If you move forward with your buddies, HIGHLY recommend creating a solid Partnership Agreement!