Your buddies first step should be to contact the FBI about what is in their system.
Find out what's in there.
CWF is a Mass term. Its used in other states, but may not be the situation in FL. So the next thing is to find out what happens to cases where an accused person completes all the requirements for dismissal of charges.
If all looks good, the next step may be to get him a Unique Personal Identification Number (UPIN) if he continues to get denied. This is typically used if your name is similar to a felon's and you are continually "delayed". But it could be used here to sidestep bad records on his actual past.
I can speak of CT as an example. In CT its called Accelerated Rehabilitation, or AR. This is offered to first time offenders of minor offenses specifically so they don't end up with a record for minor indiscretions.
The judge orders the terms of the AR. The accused meets the terms. The prosecutor nolle's the charges. After 13 months (I believe) the charges are dismissed, and here's the key part, ALL RECORDS OF THE ARREST and prosecution are purged from all reporting systems. The only records that remain are with the administrators of the AR program so that if he is charged again, they can see that he was already cut a deal.
In CT once charges are dismissed or the person is found "not guilty" all records associated with the arrest, prosecution, etc must be destroyed. Its the law. I was arrested in college and the charges were dismissed "with prejudice". The judge quite literally said to me "this did NOT happen. If you are ever asked if you were arrested, or charged, or defended yourself, you can legally say NO".
Don
p.s.
https://www.cga.ct.gov/current/pub/chap_961a.htm