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A lot of the classes that I play have Etiquette or Streetwise in their skill list, some as primary skills, so I figured it's probably best if I figure out the mechanics of this, but I can't seem to figure this stuff out.

Like, it seems pretty obvious that in some situations you want to use Etiquette and sometimes you want to use Streetwise, but even when my character has a totally reasonable Personality score, which I would think would boost my chances of success, people are still giving me the cold shoulder all of the time and I never really figured out a good system for when to use Etiquette and when to use Streetwise; they always had a really low success rate when compared to Normal speech.

All I could figure out beforehand was that if Normal dialogue tone doesn't work to just try Etiquette and then Streetwise, and this works sometimes but not reliably enough for me to bother with. Then I figured maybe it's something a little more obvious, like when you're out on the streets you use Streetwise but when talking to nobles etcetera to use Etiquette but this only seems to [&@%!] people off. I'm really confused. Is there a better system here that I'm just not seeing or am I just really unlucky with dice? Or maybe it's because having a 30 score in Etiquette just isn't as good as it seems like it should be?

I have had a very different experience. In practice, here is what I recommend. Find an NPC, then proceed to spam dialogue options at them constantly. Ask them about anything and everything. Then, once this is done, you'll see a giant jump in your used speech skill.

Generally, in my experience, using a speech skill against any NPC can only work once per conversation. After that, they'll usually have nothing to say.

I have always believed that Ettiquette is only useful when speaking with Nobles, while Streetwise is useful when speaking with the lower classes.

Since I've never deliberately improved either I've not noticed them working particularly well .

At one point I would always talk to NPCs in a non-neutral tone to improve either skill. In fact, I think you can successfully converse with commoners using the Etiquette skill too, although perhaps they will not divulge some extra information as opposed to when they trust you with successful use of the Streetwise skill.

However, I'm not sure if this entire mechanic (apart from the ability to train these skills in dialogues) was fully implemented as described in the manual. BTW, this is what the official hints page has to say about these skills:

ETIQUETTE/STREETWISE SKILLS
These two skills play a factor in several things.

TONE OF COMMUNICATING
When communicating with others, you can speak to them in several tones, which include polite, normal, and bluntly. Your etiquette skill influences your ability to speak to others politely. The better your etiquette skill, the more likely those well received from polite conversation will address your needs. Nobles and knights are just a few examples of those that demand polite conversation. The more you use polite conversation, the more your etiquette skill will develop. Your streetwise skill influences your ability to speak to others bluntly. Thieves and other uncouth sorts will respond towards this tone better, and in fact prefer it. The more you use blunt conversation, the more your streetwise skill will develop.

STANDING BEFORE A JUDGE
There are several instances where you must appear in court (i.e. killing a townsperson, and then surrendering to a guard.) If you deem yourself not guilty, you have the option to debate or lie to clear yourself. Your etiquette skill influences your ability to debate. The better this skill, the more likely the judge will set you free. The more often you debate, the more your etiquette skill will develop. Your streetwise skill influences your ability to lie. The better this skill, the more likely the judge will buy your story. The more often you lie, the more your streetwise skill will develop.

Out of the situations described above, I've only really tried to talk to nobles politely, without much success though It would be interesting to try this out with a better Etiquette skill than my character had though. As mentioned above, it seems that you can train both skills in conversations with commoners, with the equal chance that they will react positively if you succeed in using either skill, and tell you off if you don't.

AKB wrote:I have had a very different experience. In practice, here is what I recommend. Find an NPC, then proceed to spam dialogue options at them constantly. Ask them about anything and everything. Then, once this is done, you'll see a giant jump in your used speech skill.

I usually do exactly the opposite and never ask a single NPC about more than one or two topics. You know that there's this bug/feature that you can spam asking directions until the NPC will give up and mark the building on your map regardless of distance. Well, I decided that abusing this takes away from role-playing, and usually ask an NPC once, then go in the direction they tell me, after a while ask another NPC etc. until I'm close enough that they will automatically mark the building on the map. That's how it worked in Arena, and that's how you would do that in real life too (save for the whole mark on the map business of course ).

It seems that you're supposed to train either communication skill with commoners and once it's high enough try them out with nobles or underworld characters. 30% skill is pretty low, so at least something around 50% should produce higher chances of success. (In fact, I believe that the percentage actually equals success rate, although it is also modified by other stats - Personality in this case).