How to convert traditional IRA to Roth and pay very little taxes

[Nick B.]

I have recently heard of an interesting tax-saving strategy of how to convert traditional IRA to Roth while paying very little in taxes. I would like to share it and get some feedback.

In this example I'll use a traditional IRA with $100K in cash held at a bank or a broker.
I assume no transaction or maintenance fees charged by the SD-IRA custodians to make the math simple.

The general idea:

- Set up two self-directed IRAs, traditional and Roth, and fund them from the existing IRA:
  $95K goes to traditional (direct rollover) and $5K goes to Roth via conversion. Taxes on the Roth conversion are paid from cash outside of the IRA.

- Create an "Investment LLC" with two classes of shares: 5% of shares is Preferred equity (P) and 95% are Common shares (C).

- P-shares get 95% of all profits generated by the LLC while C-shares get 5%.

- Traditional IRA buys all C-shares and Roth IRA buys all P-shares of the LLC.

- The LLC invests the proceeds in something that doesn't create UBIT situation. The simplest example would be an index fund such as SPY or QQQ.

- During its lifetime the investment produces some dividends and realized capital gains totaling 100% of the original investment (this is an assumption for the easy math, actual results may vary).

- The Investment LLC distributes the proceeds as follows:
- Roth IRA gets $5K of the principal and $95K of the dividends/gains, totaling $100K;
  - Traditional IRA gets $95K of the principal and $5K of the dividends/gains, also totalling $100K

- If account owner decides to cash out and close all accounts at that point, they would get $170K in cash (assuming 30% tax rate and no penalty because of age over 59 1/2)

Tax savings:

- Traditional IRA that doubled from $100K to $200K: cash out value is $140K (30% tax on the entire balance).
- Converting the whole initial amount of $100K to Roth would cost the investor $30K in taxes.
  The resulting balance of Roth ($70K) would double to $140K - same result as in keeping everything in the traditional IRA
- As we can see, the "two IRAs and LLC" strategy saved $30K ($170K - $140K) in taxes.

The tax savings would become more pronounced if the Investment LLC invests in a high cash flow/high depreciation business instead of an index fund.
In that scenario all equity would eventually be converted to dividends 95% of which would end up in the Roth IRA.
E.g., if $100K investment produces $200K of income and no principal is returned, the final balances would be $190K for Roth and $10K for regular IRA.
Only that $10K would be taxed upon withdrawal saving $57K in taxes comparing to traditional IRA.

Questions:

- Are there any legal hurdles with this strategy? I heard it from a tax planner who sells it. Obviously he was biased and said it was totally legit. I'd like to get unbiased opinions though.

- Assuming "two IRAs and LLC" is a legit structure, what kind of business would produce reasonably high profits while depreciating original equity to 0?
  From what I understand, something like oil drilling, oil equipment lease, car wash, convenience store, or laundromat should qualify.
  If so, would they be subject to UBIT?