He wants to rent with a lady (she has 15 yr daughter) with 700+ credit score, 2x salary vs rent job, BUT she has "judgement from court" for child support services ( She needs to pay  for child support).

In the state of Florida, I was always told unless specifically shown a legal in a judgement for a property, personal judgements like credit card, car loans, gym membership judgements cannot encumber real estate.  

I know I can proceed legally towards judgements, the cost of which gets me to just over break even and i still wouldn't have any cash for my efforts.Does anyone have experience with other approaches such as collection companies or selling accounts receivablesThank for any help that you can provide

Most seem to appreciate that we care about our properties and actually work on them ourselves-- but still have good judgement about when to call in a pro.However, you really do have to be able say "No" and "Yes, I'll work the numbers and let you know how much it will cost." 

Check the records to determine if there are any liens or judgements against the property.

There are a few variables to address, but use your best judgement and make sure you have a real estate attorney do all of the paperwork for the sub 2 close and installing the lease option buyer.

I would be judgement proof.

Most likely she had a former bankruptcy, poor credit,  judgement that she is trying to hide.

This is because banks can get a judgement for payment of their losses even after foreclosure. 

I am interested in bidding on a property, I just pulled the title report for the property and it has couple of judgements from Child support services and 1 small claims.