If this is a first offense, and there was no personal injury, there is a low likelihood of jail time. However every case is specific. You need an experienced DUI attorney who works in South Florida. Review my website to see if it answers any questions you may have.
If the terms of probation is that he reports any law enforcement encounter as soon as it happens, then he should do so. Not reporting it might be a violation. Look at the probation rules and regulations.
You should have a heart to heart with your lawyer about why the State is still proceeding with the aggrevated assault. If you don't get the answer your looking for you should contact a private attorney who will sit down and carefully explain your situation. If you are in Broward county, your Judge is Cohen. He is no nonsence. It is best you speak with your lawyer immidiatly or move on. Review my website to see if it answers any questions you may have.
Your friend has rights to persue a claim for damages. Please review my web page to see if it answers any questions you or he might have. I practice in Palm Beach County and might be able to answer your specific questions.
There may be a reason to maintain a claim. You need to contact an experienced injury attorney handling personal injury cases in Palm Beach County. Please review my website to see if it answers any question you may have.
Most likely your background check will show you had a case and recieved a withold adudication. This disposition means there is no finding of guilty by the Judge. That doesn't mean that you employer will not see that, nor understand that. You can explain to them that a withold adjudication is not a conviction. I do not know if you can obtain your 440 insurance license.