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

Not to mention the tax benefits it allows. 

Of course to maximize your tax benefit it needs to be sustainable over time. 

We're right next to CA but get the benefits of no state income tax, 4th lowest property taxes, much more friendly landlord/tenant laws, no serious weather, proximity to Lake Tahoe, stable job growth/population growth, etc. 

Creative financing can help sellers make more money, solve pain points, gets them the money they need, and help them avoid a high tax bill.

Owner ended up settling with the tenant, but then we had to threaten to sue our own client to get them to pay our legal fees.- Owner must sign a Hold Harmless to indemnify us against any potential tenant lawsuits relating to the work their contractor is doing.--- Another lawsuit resulted from owner's contractor taking down basement handrail to get supplies down the steps, then they didn't put it back and tenant fell down the stairs.- We also negotiate a reasonable completion date, depending on the Scope Of Work (SOW). --- Who gets all the phone calls and wastes time calming a tenant down because the owner's contractor doesn't show up as scheduled after they took time off from work or a 3 day job takes 3 weeks?

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

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!

This might make sense, but again, you are just deferring the taxes and now pushing tax from capital gains to ordinary income. 

@Armell MayersBigger Pockets is a great place to find a real estate tax accountant.