It seems strange to me that he can't see another person that wants to see him based on a court order. I can understand not having the slag in his home or around his kids but how can the court make it illegal to shack up in a hotel room or something? Unless he's that desperate to have her next to him with the Joker (raped in the newest movie) behind them. I'm no expert on the law or anything but I've never heard of a no-contact order for two people that don't mind contacting before. Correct me if I'm wrong.
It's unenforceable and ridiculous as a practical matter. We all know that your average serious drug dealer is probably hanging out with other felons despite what any plea agreement says. It simply gives the State leverage if the person commits any future crimes.
I have picked up watching bail hearings and arraignments as my legal entertainment, and it's very normal for the judge to read off the list of probation terms and include, "No contact with co-defendant(s)." It's a very standard term. And you have people get dragged back in for violating no contact orders when both parties want contact, and the judge tells them that it doesn't matter if the other person says, "Yes, you can come see me," the judge said, "No, you can't see them," and no civilian overrides the judge.
Whether they get caught, how easy it is to avoid detection, and how strict the PO is at monitoring things is a case-by-case matter. Nick's list of potential snitches include: his immediate family (either Kayla or oldest son who promised to monitor parental misbehavior could be motivated to snitch), extended family, the law community, the Steel Toe fans, his church/homeschool community, and anyone else in the local area who he's rubbed the wrong way. This is a small town, it's a lot harder to keep things on the down-low. And doing the extra work of sneaking off somewhere far enough away that the locals won't recognize either him or April will be a more time intensive process with the possibility of drawing extra attention.
As to how much his PO is going to ride his ass on enforcement, well, we all know how much Nick loves being told what to do, and how he's a gentleman with people who he gets in a snit about... I don't think it's a stretch to think that his PO will very soon come to the opinion that he'd rather have Nick in jail than have to keep dealing with him
Of course, he won't go to jail on his first infraction, at least not for more than a day or two. He'll be brought back in front of the judge, given a higher bail, and possibly an ankle bracelet. If he and April get matching ankle jewelry, then it becomes the easiest thing in the world to know if they're violating the terms of their probation by hooking up.