I looked back at 2014 and I calculated that I've made over $43,000 in contributions to stock market investments - maxed out 401(k), Roth IRA, taxable investments, etc. 

Rather than paying yourself a commission, would reduce price or something similar to eliminate the taxable event. 

If you owned a great 2-4 unit property in a well located area B/C how would I increase profit/cash-flow and decrease expenses.  

Do you think demand for lower end properties (2/1s) will decrease over time, or be just fine.thanks,

If your prospective vendor re-sells a lead too many times, it's value to you decreases with the increased competition... so ask the right questions.Good luck!

If the rents can be raised or purchase price (significantly) decreased, you could make this work.

See Part VII - Rents, Rent Increases and Decreases particularly sections 116 through 136.Many landlords will include bills for ineligble items, or even work not yet completed that should not be permitted for an increase, so get advice from your legal representative or legal clinic on what to do.

You can purchase real estate for cash within the IRA but withdrawing funds from the IRA to purchase property would leave you with a taxable liability.

The value of the replacement property must be equal or greater than the combined "net sale price/value" of the two (2) relinquished properties if you wish to defer all your taxable gain.

I own one apartment which is netting about 7k per year income. I also am not able to itemize right now since I don't own my own primary residence. I do not have a lot of deductions in other areas. I'd like to postpone...