A friend on mine (no, its really not me) is now on probation for something unrelated to the hobby. He wants to remain in the hobby, but if he gets busted, he will violate probation and go to jail. He is paranoid that his phones are tapped and his computer is hacked.

He got a prepaid telephone, only uses the computers at Kinko's and agrees to only see well-established providers. If he is not being physically followed by LE (there is no reason he should be), should he be safe?

Given the severity of the consequence I think he should lay low-it would be pretty tragic to go to jail over this!

We don't know the severity of the offense or length of probation...  how hard he'd be scrutinized...  but phones leave records & computers leave tracks if LE wants to expend the effort.  So he's not paranoid.  
I gotta agree with Courtside, that the consequences are extreem.  That should give one pause.  
It's really hard to "keep it in yer pants" but that is probably the best advise.  The lowest risk is to follow what ever rules the probation requires & mark the days on the calandar.  

I could not in good concience encourage someone to take this added risk.  Could he even have a good time with this added stress?
skb

and hope that the authorities won't share info on what is usually a very minor offense.

Like everything else, it is playing the odds. He crosses streets, even though he can get hit by a truck.  

He should know that not every probation violation results in a recovation of probation, especially in areas like L.A. where jails are overcrowded.  Lots of "Jail sentences" are walk in, process, walk out.  This is particularly true for minor violaitons.

And that is if it gets revoked.  Often times it is not. Just a stern warning.  Depends on about 5,000 factors.

If he is as safe as you describe, it just depends how much he want to risk it.

That being said, if he is close to Nevada, it wouldn't be a bad idea.

if your on probation u usually cannot leave the state unless you work in a different state then the state you live in. If this is not the case then you have to get permission to leave the state.

Unless they have a reason (on probation for espionage, was a member of a mob, etc.), I don't think they would tap his phone just to bust him for violating probation.

Talk about taking risks, I know an escort who is on probation.

If he sticks with ladies he as seen, that should significantly reduce the risks. Just take precautions in-case she has been busted and LE is using her phone/email to bust the guys.

If he has been a bad enough guy to warrant being on probation, having to worry about engaging in sex is simply additional punishment.  Welcome to America.

yes

Dude, tell him to lay off the Hobby for awhile.

Put it this way, is a piece of ass WORTH going to jail for?

Then, tell him to start using one of the Popular dating sites.
2x out of 10, it's like shooting fish in barrel.

Just got to find the right "2" to go out with.
(hint: if in her profile, she's got pictures of herself on her bed. In any fashion, clothed, whatever...She's looking to hook up! Dead give away).