First, as you're a Southerner and I'm a Yankee, please take into account the cultural differences. I don't know what they might be, but I suspect that approach to conversation is very different in subtle ways.

You don't have to be bragging unless you start out with, "I have this big pile of money I just don't know what to do with. If you had a big pile of money, what would you do with it?" The underlined phrase is the mistake. There is no "if"; of course the person you're talking to has a big pile of money.

One possible opener might be: "I have a kind-of happy financial puzzle. You always look like you're doing well, and you're a smart person whose opinion I value. Would you mind giving me your opinion about this?" A little flattery, especially as it will be sincere, will go a long way to innoculate you from being thought a braggart. You also don't have to be the first one to mention the dollar amount. Let them ask you.

Don't expect a whole lot from the first contact. It's just a short casual conversation. Research any suggestions they make, and then talk to them about your findings later. This will show them that you took their suggestions seriously (putting weight behind the "valued opinion" phrase), and will give you the opportunity to share information that they might find valuable, a quid pro quo. The conversation can procede from there.

If there are several people whose opinions you might like to solicit, you can approach them all individually, and once you get a series of dialogs going, maybe suggest that you all have lunch and talk about your mutual interest. Then you have a support group. Remember you are only the host, not the chairman. The natural structure of a support group is conversational, not corporate. A wise host will also steer the conversation in extra-topic directions, like sports, barbecuing, lawn care, and so forth. People are more likely to share sensitive information with people they consider friends. Information about money is always sensitive.

This is the perfect time of year for discussing finances. People are often touchier about their wallets than their sex lives, but from now until April, lots of people will be complaining about their taxes and/or financial aid applications to get their kids' college tuition taken care of. It's the one time that everyone is willing to talk about money in general. It wouldn't take much to turn it into a conversation about specifics, one-on-one.

If you approach people individually, they will be less likely to be leary about exposing their financial experiences than they would in a group. If you treat your potential advisor like an equal, or even a mentor, you won't come off looking like a braggart. The flip side: Don't act like a supplicant, either: people will wonder what you're up to. (The oily and obsequious Uriah Heep is the least trusted character in Dickens's whole body of fiction.)

Never talk about what one person said to you to another person if you're doing the multiple-chat-up thing, lest you be thought a tell-tale. Your conversations about money will dry up immediately if people think that. You can, however, mention you've been talking to so-and-so, who "has some interesting ideas", or who "agrees with you". Your advisors never "disagree"; they "have different ideas". At this point in your group development, variety is good; disagreement is bad. If two people are going to disagree, let them discover it for themselves, in person.

To introduce one person's name into the conversation with another person is the step just before the lunch invitation. If someone expresses curiousity about the ideas of someone else you're talking to, you can say, "He/she explains it so much better than I can. Why don't I see whether we can all have lunch, and he/she can tell you him/herself?" If no one is curious, you can take the bull by the horns and just invite everyone yourself.

Maybe this will work for you. Good luck!