Without income and existing homes it will take extremely deep pockets to make it profitable and a very long time.

But also not sure if you are able to keep any of the profits or do you roll the entire amount from one to another?

If you can save enough for down payment, closing costs, and an adequate  buffer than by all means move forward in trying to meet your real estate investment goals.Will the duplex in Chicago cash flow and if not could you sell it for a profit and then reinvest that money in the San Antonio area?

IE $5k+ for not paying 8 cents.Regardless, unless you have a TON of units, with rates as low as they are there isn't much "profit" to be made.

@Danny Webber@Brandon Miller Yes you both have a point its more steady and i see more flips with more profit In San Antonio Where most of the jobs are more diverse and don't rely so heavy in oil Industry it seems riskier for me or at least those are my thought in the las crash in 2015 I saw so much of the population move out and real estate dropped so much it became a buyers Market with the low prices everyone was moving out due to job loss or lay offs  

@Dmitriy Fomichenko I was under the impression that the IRS considers all 'flip' profit as earned income per se???

One thing I cannot find though is how to turn a profit on renting real estate with a mortgage using a 20-25% down payment.

Or allow the individual to partner and take an equitable share of the profits until I can pay them off. 

Cashflow is bigger.Profit is bigger.Done right, management is actually less than houses.I typically make $400K-$600K profit per multi-unit apartments, in addition to the cashflow on a monthly basis.

I'd look at a CPA Audited tax returns and CPA Audited profit & loss before going forward.