That question cannot be answered in definite terms. 

I guess I'm missing something here...it seems like I'm stuck putting money into this system indefinitely.

This isn't merely about replacing your current income—it's about creating an income stream that sustains your lifestyle indefinitely.

A 1031 exchange is a great way to indefinitely defer the tax and use it to grow your RE portfolio, and build long term wealth.The most important factor in a 1031 exchange is that your qualified intermediary must be in place prior to the closing of the sale of your old property.

Especially with the favorable tax incentives offered to buy and hold real estate vs the ordinary income tax you'll pay on private lending.A 1031 exchange would allow you to indefinitely defer all of the capital gains tax you would have to pay, and instead use it to purchase better performing property/properties.

@Jake Hughes A 1031 exchange is a great way to indefinitely defer all of the capital gains taxes, and gain access to that tax to use over time for your own benefit.

The 1031 exchange would allow you to indefinitely defer all of the capital gains taxes and use it to purchase multiple newer properties with lower capital expenditures, in a better market. 

Under current rules, NOLs can only be carried forward indefinitely (not carried back).Losses from stocks (Schedule D/Form 8949) follow different rules and cannot be mixed with Section 1231 losses.

I am able to bear the economic risk of an investment in the Shares for an indefinite period of time and understand that an investment in the Shares is illiquid and may result in a complete loss of such investment.Was that in their agreement and did you sign it?

This method allows you to take some of the profit tax free and indefinitely defer the rest of tax, using it to purchase larger, nicer property/properties in areas with better cash flow potential.