What is the biggest pain point when it comes to your finances?

Fortunately, I have planned well for retirement. However, what many in the military fail/are unable to plan for is divorce. Like most LTs, I received my briefings on the 3 legged stool (Insurance, Savings and Pension). I balanced these well and despite the influence of divorce (division of property, equitable pension pay-out, child support and alimony), I may outlive my finances. But too often, I have bumped into the veteran/retiree, who has been stripped of everything, including his dignity after divorce. If you are writing a wealth building course, include the value of a pre-nup to your discussion as well as the limited influence a pre-nup has on the government mandated former spouse protection (pension payout). Good luck.

My biggest peeve is when they give you a hundred dollars and take back 99.

Investments, by far. I've found that basic "program" investments such as 401k, 529 college plans. etc. Just don't show much return. In fact, here's an example: My daughter's 529 was doing OK until everything crashed out in 2009, then it took a few years to even gat back to the level of the deposits, and never really performed after that. After well over 10 years of deposits, it's barely above the amount of the deposits. Several years ago, I stared a plain old educational savings account, and after continued non-performance of the 529, I cut the deposits to it by 75%, and deposit to the savings account, because it just plain performs better. The kicker is that the 529 is with USAA, where investment accounts are actually fairly highly rated.