So, on a $200,000 house I get $20k Option fee non taxable cash, up front. 

Generally, when you sell it is a taxable event. 

At the end of the day, it's really all about the leverage and how efficient one can be with generating cashflow out of any one property (like with utililzing HELOCs for example or to take advantage of depreciation to offset taxable income).I know we're on BP but this is why Alternative investments in addition to my company and their vertical are so important for my personal cashflowing needs.

My understanding is that they can't touch the money or the profits themselves without a taxable event so they have to have a non-family member handle the transaction.I can point you to a company that sets those up if you don't have one already. 

But -- contributions lower your taxable income. 

100% taxable. 

It reduces their taxable income and gives them a steady paycheck without any of the responsibility.

Assets in your taxable non-retirement accounts can be sold for a profit (unless you bought everything last November) and hopefully as long-term capital gains.  

If that will bridge your transition period, it might eliminate needing to take a taxable distribution from the current IRA.Another option is a Rollover as Business Startup.  

Regular monthly maintenance on an STR property can be deducted from taxable income?