How should I...? vs. How would I...?

It sounds to me like should and would can be interchangeable in that second example. As far as I am concerned, both would express the same thing. Fun thing to remember (I don't know if it's related or not): should is [technically] the past tense of shall, whereas would is [technically] the past tense of will. When I say "I will eat soon," I mean more or less the same thing as when I say "I shall eat soon." Though of course, historically, these verbs carried different meanings.

"How would I go about helping my brother get some help with his drug abuse and violent behavior?"

See, I find that "would" and "should" would (heh) give the sentence a different meaning. Putting "would" in there sounds as if the speaker is seeking a formula (you would call, receive an operator, leave your number, etc.). "Should" seems like speaker is looking for personal suggestions (find out what you can about resources, be open for him to come to, etc.)
"How should I help him?" Well, you should be supportive.
"How would I help him?" Well, you would contact xyz.

These might be minor (possibly incorrect) observations of how things "sound." Thoughts?

first, being from the south. We'd never say:

"As a Southerner, how would I be received?"

We'd say, " Bein' as I'm from here, how'd you take me?"

second, I can't believe i just read this!

Hey brandon,

You're still using "would," as "how'd" is a contraction of "how would." We're all still very happy that you're proud of your regional dialect though.

too funny... my wife would like this site, I think I'll send her a link.

Would makes it a hyothetical situation. You're setting up a condition. You're not asking what you should do, which sounds like you are asking for recommended methods or polite methods or what you could do. You're asking what you would have to do in order to make sure that your brother definitely gets help in not so many words. That's just how I see it.

"How would I go about helping my brother get some help..." implies an uncertainty of purpose or a condition to be met: "how would I, if I were to choose to do so?"

"How should I go about helping my brother get some help..." implies a certainty of purpose, or an unconditional intention: "how should I, when I choose to do so, or now that I have chosen to do so?"

Although it's quite common these days for someone to use 'would' when they are in fact certain, it's best to bear in mind that 'would' implies a follow-up 'if' condition.

1st Person: Shall is future; will is determination. Reverse the 1st person rules for other persons.

"'ll" means either "shall" or "will." "'d" means either "should" or "would."

I'd never contract "should" as 'd. You'd never do it either. (I mean you should never do it :)

On the sentence about the brother with a drug problem: I consider "would" a request for a general procedure, "should" a request for specific advice. For extra fun, I just read a paper on the difference between the modals "will" and "be going to". Consider "We will change your oil," a polite offer seen on an advertising billboard; versus "We are going to change your oil," an obnoxious declaration of a future fact that would drive customers away.

... and then there is this usage of "should"--
"What would you say should I decide to arrive earlier than planned?"

morals (should) and morés (would)

"As a Southerner, how would I be received?"
I don't know but I'm contemplating non-Southerners' ways, leaving them open-ended to how they _typically_ treat Southerners BY CONVENTION, a case of mores. To say "should" implies some moral expectation by you of them and their attitudes towards you, even if you yourself are unclear on those morals.

"How would I go about helping my brother get some help with his drug abuse and violent behavior?"

In both cases, "would" implies not only morals held but actions to be carried out. Since your relationship with your brother is, I presume, closer than with non-Southerners, "would" is more appropriate.

"Would" suggests "not only should, but I shall in deed (action)," as a moral imperative of futurity.

"I would if I should."
"I shall when I can."

when ordering from a server do you say; " I should like..." or "I would like...." it would seem to me if you have never had what you are ordering then how do you know you will like the food or beverage etc.? please assist, thank you.

Just eat, when someone says "I would like the soup, please", that doesn't mean that they think they are going to enjoy the soup. It only means that they would like the server to serve it to them:

"I would like the soup, please" = "I would like [you to bring me] the soup, please"

"Should" often means "supposed to", bur doesn't require the action to be carried out. "would" often describes an action that will be carried out, but is conditional.

"I should eat more vegetables" means that it would be good for me to eat more vegetables (because they're healthful, and maybe I don't eat enough of them). It in no way means that I am actually GOING to eat more of them.

"I would eat more vegetables" is more assertive, but conditionallly so, as in, say, "If you steamed them instead of boiling them, I would eat more vegetables". It means I would definitely eat more of them, but only if you steamed them first.

If there were no conditions, then I would just say "I will eat more vegetables".

mmmmmmm, I like vegetables.