To get a realistic apples-to-apples comparison - and to see how very difficult this hindsight exercise is in real life - compare a 30 year stock basket to your RE example.

Consider setting a daily exercise & study schedule.Philanthropy: May I be so bold as to suggest that you have a responsibility to give back?

I didn't think this exercise was going to actually result in my wanting to take next steps, so I thought I would post this here for some feedback.  

It is meant to be a simple mental exercise in evaluation of return, that is all.  

I usually met people as a paramedic at the tail end or somewhere close to the tail end of what were usually a long series of bad choices, sometimes a short series of bad choices, occasionally just plain bad luck.Our choices on all aspects of life are cumulatively profound - health, diet, exercise, realtionships, happiness, anger.

A creative solution might be leasing to a tenant with an Option to Buy which they can exercise once the two year redemption period is up and/or consider seller financing (both with full disclosure and documentation of course ). 

So it becomes a mental exercise to convince yourself you are feelng excitement.

You and the seller transfer a deed and also at closing the documents have the wrapped mortgage subject to the existing note in place.You need to set a third party servicer to handle your payment so that the underlying mortgage will be paid and the rest goes to the seller on the wrap.You will run into property insurance issues and possibly the bank on the first mortgage exercising the due on sale clause.

Which over time , as a cumulative exercise,you could be well on your way to income replacement and beyond.Sometimes,look outside the square!

If you have a lease with an option, why dont you assign it for a fee and have the new tenant buyer open up a CD with $10K a month, then exercise the option when it hits the amount needed?