Question: (Matty, Chandler, AZ) I work at a small family business making 100K and we have a bad SIMPLE IRA managed by a third party making high commissions. (I have tried to switch plans and do the leg work, but they have friends in the business and are resistant to changing) The funds available have 5.75% load fees or 2% yearly management fees and there are no good options. All I want is some low-cost index funds or TDFs (target date funds) that don’t have exorbitant costs. I have read that after 2 years from my first contribution, I can roll over my balance to a rollover IRA while still employed. Can you shed some light on this strategy and any possible pitfalls? I love my job and want to continue working here for as long as I am able. I will max out my SIMPLE this year (and max my Roth, my wife’s Roth, and our HSA) but want to take advantage of the tax deferred dollars without getting crushed by fees. I am hoping to rollover once per year and continue working at this great job. Secondly, can I roll this yearly to a Roth and pay the taxes yearly to stash away some extra Roth money? (Roth conversion) I am 33 married and have a 3 YO and 1 YO. We are doing great these past few years but just started investing a few years ago so I am trying to catch-up a bit and set ourselves up for a bright future. My income may continue to go up and I would like to get a good stash of Roth dollars if possible.
• Simple IRA balance $15K
• Roth IRAs $40K
• HSA $12K
• Brokerage Account $25K
• Homeowner with $250K equity (until the market crashes)
Thanks for all that you do, my wife makes fun of me for listening to YMYW but appreciates its value.

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