Nice topic/discussion with actual examples on what is required to acheive such a tough goal.I often think about trying to move into cash flowing properties full time but realize how tough it actually is to achieve and work involved.I have a nice supplemental income from it and continue on working on increasing my NET monthly + cashflow from my properties but kind of took a step back and am not trying to do this solely now.

It sounds like you had plenty of foresight early on that RE investing would supplement your retirement.

If they do $5 MM in loans every year, they can make an additional $50k to supplement their salary which is huge for them.But, at the end of the day, the underwriter makes the final decision on loan approval.

As a new owner this is the best time to make changes.Whether you wish to collect market rent from your income property to maximise your investment or continue to supplement your tenants rent depends on the direction you want for your future.

My goal with real estate is not to quit my job (I love my career in medicine and plan on sticking with it), but rather to supplement my income.

I currently have a 9-5 job as a Software Developer and I was just looking for a new hobby that may also bring in some supplemental income.

I will also be looking into some umbrella insurance plans as well to supplement. 

There are just too many expenses to be an agent to be able to make it with no experience and no cash cushion or another job to supplement the income.

I'm a complete newbie interested in slowly obtaining long term properties to rent out and supplement my income when I ultimately retire (in around 20 years). 

I had to make a business decision to either continue to supplement it at $750 per month for how many years and HOPE that not only would the rental rate increase, but also the equity.