How do I set a realistic goal to retire on rental income?

[Justin S.]

I am 38 years old

My goal for the past two years has been to retire on my rental income

I am having a huge struggle as to how to obtain this goal.  I own another business where I am the main draw of the business so I need to make sure I can cover 100% of the income I make from that business and then some.  (estimated 90k/yr)   I don't believe working there less or not at all and keeping the business is an option.   

I am fighting between two options 

1. Buy as many units as possible to be able to make that 90k even while the properties still have mortgages on them.

2. Stop buying and pay off what I have now as quickly as possible and that will bring me anywhere from 89-110k per year.  This doesn't sound like fun to me but I love the feeling I get when I think of all of my properties free and clear,(I'm smiling as I type that)

I feel as if option 1 will take longer but when the mortgages are eventually paid off, Ill be lovin' life! 

I feel as if option 2 could happen sooner but then all I have is 89-110k/yr.  Of course, I could start buying again after all of my existing properties are paid off in 5-8yrs

This needs to be 80% financial decision,20% emotional/mental decision.

Thoughts?