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mc, hat is off to you for taking these steps to make your financial future better. I have a couple of thoughts, but generally echo rad's first response to your post (more on that at the end).

I started a non-retirement investing account to learn more about the stock market and put some extra money in savings to work.

All of the advice I've ever gotten, and all I've ever done, is to make sure all tax-deferred options for investing are maxed out *before* starting anything that's taxable. Even an HSA (triple benefit!), if you're eligible. Depending on what you plan to use the money for, "tax-deferred" doesn't automatically have to mean "can't touch until retirement age". Emergency fund, one-time home purchase, and other uses are potential exemptions to taxes and/or penalties in IRA or similar accounts.

Does the amount I have contributed to the traditional IRA vs investment gains matter when determining tax implications for a rollover [to Roth]? Or do taxes simply relate to the total in the account at the time of the rollover? Would that rollover amount contribute to our overall income for the year?

Pretty sure it's the second one, and yes. I was also under the impression when the Roth program began (1998?) that you can only exceed the annual Roth contribution limit by doing a Traditional-to-Roth rollover *once*, so parceling out that $60k you mentioned over multiple years to avoid the marginal tax bracket bump might not be an option. And I'm nearly certain it would be expensive for you (that particular bracket jump is big, IIRC). I haven't kept track to see whether that rule has changed since the early days.

So, we rolled that money into a 529 account in my wifes name with the plan of switching it back to our daughter once she is off of Medicaid coverage. Are there any tax implications for this move? If we are making or will make contributions towards this account this year or next will that change anything tax wise?

No tax implications... your wife and daughter are basically equals under 529 rules. It's basically an 'education Roth' with looser rules in a couple of areas, including which family members can contribute and benefit. The one thing I learned over the years with 529s for my own kids though, is that *rolled* is more accurate than *switched*. Neither institution I've held them with has let us just swap out the 'student SSN'. As you probably saw, it's a whole new account number your wife now has, and when your daughter needs that money, her account will also be set up as a new one to receive the rollover from your wife, rather than the original one you opened--in my experience they only 'roll forward'.

So, I'll let others address the other 4, and certainly hope someone can correct me where I wasn't right, but here's the "Consult your tax advisor" part: I had a detailed tax question that this website wouldn't let me post here for some technology reason, so I ended up meeting with a basic strip-mall tax dude from H&R Block to get answers. I made an appointment for 2 days after my call, sent my questions (a detailed list like you posted) to him in advance, and spent the money. Sort of (he refused to accept it). Their rate was $30 for a half-hour sit-down, $50 for an hour. It took under 20 minutes, and at least 5 of that was about football. Given how much money you'll save in taxes with the situations facing you, that will be money VERY well-spent. If you're averse to Block or have a tax person available through your financial advisor (they're rarely the same person, or even firm), you could surely contact someone else. I used Block because the two other places I called weren't taking new clients and didn't want to do a one-off Q&A anyway. But I found them plenty confident about the "taxes" part of investing. Regardless of where you get your advice, I hope it goes well!

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