With a $100K, 33% down, mortgage instead of a $180K mortgage, 20% down, I manage to snag a property where the rent of 2 units covered the mortgage and taxes, and I house hacked for free.

From the nightly rates you can estimate the monthly income, minus tax, insurance, cleaning fee, ect. ect.

buy low sell high  sell for cash for carry contracts.U find land at Tax sales a lot of the time. or you use whatever direct marketing concept you can afford  direct mail telemarket etc.you need great phone  and closing skills .. anyone can get leads but without closing skills your success rate will be limited greatly. 

Proceeds from that sale are tax deferred and it made buying up on an asset easier.

Of course when you look downtown the home prices get much higher, however, there is a historically redlined area, that is still very close to downtown, and just because it's on the west side of the freeway and houses are less taken care of, you see homes for less.Developers are quickly snatching up properties because of this reason and because recent zoning laws have done away with single family zoning, so I'm feeling a sense of urgency to get into a home in this very specific neighborhood.I'm not a super personable guy and feel strange knocking on doors, so I started digging into delinquent taxes.

They would pay the taxes, insurance, HOA and all maintenance/repairs, and I would pay the P&I. 

@Vi Prich if you lived in the rented one 2 out of the last 5 years, you can keep up to $250,000 single or $500,000 married equity tax free.

This all depends on the numbers and I suggest a tax advisor.

Law: Illinois has a law that requires (I believe) the insurance company to give a 'General and Special Taxes & Demolition Expenses' Form (Important info for this issue) to the city when claims/damages are over a certain dollar value.

From a purchase and tax standpoint, I would operate the business expenses as usual in the name of the LLC as previously done.