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

You are looking at the rent of $2,000 and mortgage (Loan, Insurance, and Taxes) of $18000 and thinking you have $200 cash-flow.

Also, I believe the tax benefits are horrible compared to the states, but I'm not too sure.

.🔹 Property Tax Relief – If your property is severely damaged, you may qualify for reassessment and potential tax refunds.

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!

There are also some tax advantages to self-managing. 

Technically it would be best to get a C Corporate or S Corp. to flip properties and since you are considered a dealer if you do several properties a year and this could have negative tax consequences in an LLC.

Consider using an FHA loan to secure a 1–4 unit property with just 3.5% down and take advantage of tax benefits by living there for at least two years.

. - Fortunately, our transparent systems allowed the owner to catch it:)- Full transparency - we would have never caught this honest mistake:(An owner also needs to be involved to approve & fund large expenses: maintenance, property tax & insurance payments (if they want to be more hands off), evictions, etc.A great PMC should also have a chat with you annually about your future plans for a property and your portfolio. 

That immediate tax savings in the new property is better than the infinite tax deferral of the 1031 exchange.