We also (unwisely, in retrospect) borrowed $45k to help expedite the renovation, so we 'owe' $345k in total. 

In retrospect I regret selling it because the income was so good, but sometimes short term profits are too good to pass up, and it basically paid the entirety of my daughter's 4 years of college on the spot. 

There is never going to be a perfect time to invest, that window is only evident in retrospect.  

In retrospect, I suggest the following:1.

In retrospect, I think that was unnecessary.

Have any of you made a transition from owning a ton of properties, to private lending and wish you made it happen sooner in retrospect?

My gut instinct told me that much of what I was 'taught' was wrong.To confirm or deny my gut instincts, I conducted a retrospective analysis of my portfolio against three common tenants of real estate that I was 'taught'.   

In retrospect I wish I had kept doing them myself.  

In retrospect I actually should have done what you did and required for one of the units to be vacant at closing.

Is there anything you would have done differently in retrospect?