I have no idea about probation in Rhode Island, but it's a northeast state, and I assume more judicially liberal than say Mississippi. I would be surprised if he went to jail. If he does, it will be because of the heinousness of the charity angle. If he stole 3k from anything besides a charity, him going to jail wouldn't even be in the conversation imo.
In Pennsylvania, I knew a few people on probation, and it's absurd. A guy I knew was convicted of vehicular manslaughter for killing his best friend while drunk behind the wheel. Real asshole. He got pulled over routinely for driving w/out a DL, as he'll never have a license, and never was jailed. He drank, posted where he was drinking on facebook posts, etc. Nothing ever happened. He was also a heroin addict in addition to being a drunk. He would come up dirty all the time for both alcohol and heroin and was out driving around, getting into trouble. His probation officer only acted on a 3rd strike every 6 month period. So essentially, unless he flunked 50% of his tests, nothing ever happened. He died this past month from a heroin overdose, so he won't be out drunk hurting anyone again, but I always found PA's probation absurd. Ohio is much quicker to violate, but PA is like many of the northeast states in their approach. For those looking to see him incarcerated, temper your expectations. It's possible, but I wouldn't bet on it.
The father of the girl with this disease is certainly the best person to bring a little heat to an overwhelmed probation officer.