Those layers of worries have altered the way financial advisers are serving credit union members. Once upon a time, a conversation would include talk about annuities and rates of return. Now, it can be dividing assets among divorced boomers who cohabit under the same roof. McGlamery has been involved in the latter.

“They're still living together to survive financially. Normally, I'm just advising one (person in the couple),” McGlamery said. “In these situations, I'll ask about income, how much you owe on your mortgage, how's the cash flow. Every situation is unique.”

McGlamery and two other advisers travel between Vantage West's 17 branches to meet with members. The credit union's investment program has been around for roughly 15 years but in January, Vantage West Financial Advisors partnered with CUNA Brokerage after leaving a long-time alliance with a leading broker-dealer. The division has $70 million in assets under management, according to McGlamery. Business has been so brisk that the program is looking to hire a fourth adviser, he added.

Vantage West was chartered in 1955 as DMAFB Federal Credit Union to serve military and civilian personnel working at Davis-Monthan Air Force Base in Tucson. Many of the members are retired military like McGlamery, a former Navy pilot who transported people back and forth to carriers, and the bulk of the adviser program's clients are in the boomer age range.

“Vantage West has many loyal members who are baby boomers,” said Bob Ramirez, president/CEO of the credit union. “Making investment services available inside Vantage West branches continues our legacy of community banking, while at the same time injecting financial investment muscle and expertise into the mix.”

The good news is more members are in a position to retire and maintain their current lifestyles, McGlamery noticed. For those who have to work past retirement age, they're doing so with paid-off mortgages and less debt.

“When you retire, it's just about cash flow. There aren't a lot of pensions out there now. For some folks, it's just savings and Social Security,” McGlamery said. “The key is to get your debt paid off. You may be at a point where you will have to work part time.”

Read more: The Great Wealth Transfer

Over the next 30 to 40 years, boomers will transfer $33 trillion to Gen X and Gen Y, according to The Great Wealth Transfer, a 2012 report from Accenture. McGlamery said he is definitely seeing an increase in inheritance transfers. One of his first clients, a 90-year-old member who recently passed away, left a substantial inheritance that is currently being divided up among three children.

For those that see Social Security as their primary means to live on during retirement, McGlamery said he's most concerned for the generations coming after the boomers.

“I read that by 2033, the Social Security trust will be dried up,” he noted. “Gen X will have to pay taxes into that trust fund. I call it a pig in the python. It's moving along slowly but at some point, it will need to be addressed.”

Social Security is a huge concern for some of the boomers at the $598 million Red Canoe Credit Union in Longview, Wash., said Helen Alexander, vice president of wealth management and a CBSI financial adviser. So much so that it continues to be a hot topic at credit union quarterly seminars and during on-site sessions at select employee groups.

“There are stages of their concerns, especially when (boomers) are getting to retire. They want to know if they're going to have enough to live on,” Alexander said. “They've been in the mode of saving for so long but now, they're not sure how to get to it.”

Alexander said some members who work with Red Canoe's team of financial advisers tend to fall into two groups: those who've saved and are petrified to spend and those who have so much money that they think it will last forever. Depending on their situation, she may have to give a nudge to those in the first group to reassure them that it's OK to use their savings – even it's for a little, fun splurge. For the spenders, a hard discussion on clamping down typically brings them back to financial reality.

Besides Social Security, healthcare expenses are another pressing issue for some Red Canoe members, Alexander noticed.

“Over the last year and a half, health care reform has created a lot of confusion,” she said. “Some companies that used to provide health care for retirees have stopped. We're teaching (them) how to navigate the state of Washington website to apply for coverage.”

Another growing trend is adult children who need more financial support to care for their parents or to pay for assisted care facility costs, Alexander said. On the flip side, last week, she met with four clients who were raising their grandchildren but didn't plan on the new role at this point in their lives and were in dire need of financial assistance.

Like McGlamery, Alexander said she is starting to see a steady stream of inheritance scenarios.

“It's a little overwhelming for some people because they say, 'what do I do with it?' They want to honor it because their mom and dad worked hard for it. So, they'll do things like pay off their debt or help their kids pay off their debt. I may have met with one or two clients that were like, 'Woo hoo, let's have a big party.'”

Red Canoe's adviser program has been around for more than 15 years and has $100 million in assets under management, Alexander said. Roughly 50% to 60% of the program's clients are boomers, she added. At first, she would either meet with a male client or a couple. Now, as clients get older, she's seeing more females who come alone or have taken over handling the finances because their husbands don't have the mental capacity to do so.

“With a lot of the women, they have this fear that they will be impoverished. Much of my job is educating them on what they have,” Alexander said.

Indeed, women are outliving men and the questions they have such as when to start drawing on retirement benefits continue to weigh heavily on their long-term planning, said Terry Colen, CBSI senior financial adviser and trust liaison officer at the $1.7 billion Truliant Federal Credit Union in Charlotte, N.C.

“Longevity creates health insurance issues. They want to know 'when do I take Social Security,' 'when can I touch my IRA,' and 'do I even have enough money set up in retirement,'” Colen said. “Financial planning becomes risk management.”

In place since 1995, Truliant's financial adviser program has amassed $190 million in assets under management, Colen said. Seven salaried advisers work with members and nearly 70% of those clients are in the boomer age range, he added. Many of them are engineers and expect top-notch expertise, he pointed out.

Biggest issues for Truliant's boomers: how to navigate Social Security and health care costs. Members need hand-holding when it comes to the Medicare and Medigap maze and the conditions on when to take certain parts, and how leaving an employer can lock up any chances of getting in during an open enrollment period. Colen said monthly seminars address these topics along with long-term care and trust estate planning.

Colen has a startling way of helping boomers see the big picture.

“As advisers, we should kill them, fire them or have them live to 100,” he explained. “By that, I mean if you die tomorrow, who gets your kids? What if your spouse dies? Do you have a will? If you left your job tomorrow, how much money would you have to live on? Do you know anyone who is 80 or 90 years old? How much will things cost when they reach 100? They come in for retirement planning but we want to do life planning.”

Colen said generally, he only sees inheritance situations in cases of premature death. What's more prevalent is when a boomer has a special needs child or ensuring beneficiary designations are up to date, especially in blended families.

“When I started out 25 years ago, it was the best annuity or rate of return. That's irrelevant. Now it's, 'How can I make sure that my grandchildren are taken care of if something happens to me.'”