BIG DISCLAIMER: I AM NOT A LAWYER.
I'd suggest taking at least a couple pistol classes if you can possibly afford to. NRA basic handgun at the minimum, and if there's a concealed carry class nearby, definitely look into that. Include documentation when you mail the judge. Explain that you've taken the classes and would like the restrictions removed. IMHO, you shouldn't explain why - just ask for them to be removed. Alternatively, write to the judge before doing anything and ask what he would like done in order to have the restrictions removed. It may end up being as simple as "ask for it".
There is no basis in law for the restrictions placed on permits by judges, but court cases have upheld their authority to do so. (Imagine that, a judge upheld another judge's authority.) Can you carry all the time with it? Legally, yes. The worst an officer can do is contact the issuing authority and explain why you should have your permit suspended or revoked. It's up to you if the risk is worth it.
If you are carrying on a restricted permit and get involved in a defensive use of your gun - even if it's 110% clean - expect a crapstorm. A good (slimy) civil lawyer will catch on to your permit being restricted and put that in front of a civil jury in a heartbeat. I'm sure you can imagine where that goes...
I did carry sometimes on a restricted permit for a while. I had a relatively civil discussion with one of the local officers about it and no repercussions. Then I moved to a neighboring county, which doesn't do restrictions at all, and transferred my permit. Now it says on the front "for the purpose of CARRY", and I'm armed 100% of the time.
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