Honestly if your city has a 311 style thing, I'm not sure there's a ton of need for an LLM. Eight or nine years ago my grandmother visited me in New York and accidentally left her pocket book in the cab. Since I had paid for it with my credit card, I was able to see the medallion number in the transaction, so I called 311 and said that I wanted to get in touch with a specific taxi. It prompted me for the medallion number, which I told it, and then it transferred me to a call with the dispatch service, who then transferred me to the specific garage, and they called the driver and told him to call me, so we were able to meet up again and get the pocketbook back (turned out he returned to where he had dropped us off to try to find us, but since we only had a short stop there, we took another cab back to her hotel after, so we were gone).

This works fine when you're sicking enforcement on someone and don't really care, the bigger the blast radius the better, you just want to know who to call.

Where it falls apart is "how do I" type questions because usually the legally factual answer is some huge complex state diagram where three local and four state agencies theoretically have discretionary jurisdiction over a your petty af project or business but the in practice answer is that some agency rubber stamps them all with minimal fuss. You can't make the legally factual answer clear because the degree to which people support the status quo is largely predicated on ignorance, but you also can't come out and say in writing that you have a policy of rubber stamping boring stuff.

Basically the same reasons that all but the most minor and narrowly targeted attempts at permitting reform fail.

The thought is nice but in reality you're basically asking the government to give up power and it takes obscene amounts of political capital to force that to happen in most cases.