Something no one has mentioned yet - have you considered using a Self-Directed IRA LLC (sometimes called a checkbook IRA) instead of ROBS? It might be better suited for real estate investments and doesn't require setting up a C-corp or dealing with the active business requirement. The downside is you can't personally benefit from the properties or be involved in day-to-day management, but for pure investment purposes it might be a cleaner structure. Just make sure you understand prohibited transaction rules because they're strictly enforced.

I've been following this discussion closely as I'm considering a similar structure. One thing I haven't seen mentioned is the potential impact of the Corporate Transparency Act (CTA) on ROBS structures. Since your C-corp would likely be considered a "reporting company" under the new beneficial ownership reporting requirements, you'll need to file FinCEN reports disclosing ownership information. This adds another layer of compliance but shouldn't affect the tax treatment of your ROBS. Also, regarding the LLC structure you mentioned - make sure you understand how the K-1 income will be treated at the C-corp level. Since C-corps don't get pass-through treatment, the rental income will be subject to corporate tax rates, and if you later want to access those funds personally, you'll face potential double taxation through dividends. Have you considered whether the rental income strategy makes sense given that corporate tax treatment, or would you be better off with a structure that allows pass-through taxation?

Has anyone dealt with state tax treatment of these charitable annuity distributions? My federal return was fine but my state (CA) didn't seem to recognize the charitable aspect and taxed the full distribution.

This is a really complex area that trips up a lot of people! I went through something similar last year with my non-qualified annuity. One thing I learned that might help - make sure you understand which portion of your distribution is taxable gain versus return of your basis (the money you originally put in). For non-qualified annuities, only the earnings portion is taxable, not your original contributions. So when you're calculating how much to exclude from taxable income due to the charitable contribution, you need to work with the taxable portion only. Your annuity company should provide documentation showing this breakdown. Also, definitely keep detailed records of the direct payment arrangement with your annuity company. I had to provide a letter from them confirming they made the payment directly to the charity per my instructions. The IRS wants to see that clear paper trail showing you never had constructive receipt of the funds.

Has anyone tried just not checking the waiver box? I underpaid last year too (about 20k short) because of unexpected consulting income, and I just calculated and paid the penalty. It was like $700 on a $20k underpayment. Seems easier than trying to get a waiver approved.

I went through almost the exact same situation two years ago with stock sales! Here's what worked for me: I did include a written explanation even though my software didn't require it. I kept it simple and focused on three key points: (1) this was my first time dealing with significant investment income, (2) I wasn't aware of the estimated tax requirements for capital gains, and (3) I paid the full amount owed when I filed my extension before the deadline. The IRS accepted my waiver request. I think the key was showing that I acted in good faith by paying everything as soon as I realized the issue during tax prep. Don't just say "I didn't know" - emphasize that this was an unusual circumstance for you and that you corrected it promptly. If your software won't let you attach the explanation, you can either mail your return instead of e-filing, or e-file and then mail a separate letter referencing your return. I'd definitely recommend trying for the waiver since your underpayment sounds substantial and the penalty could be significant.

I work in banking (not for SBTPG) and can share that ACH transfers follow standard protocols regardless of the sender. Once the IRS initiates the transfer on your DDD, it typically takes 24 hours to reach SBTPG. I received my DDD on February 26th this year, SBTPG showed funded on February 28th around noon, and the money hit my bank account on March 1st. This 2-3 day timeline has been consistent for me across multiple tax years.

As someone who's been using SBTPG for several years now, I can confirm the 2-3 day pattern most people are describing. What I've found helpful is understanding that there are actually three distinct phases: 1) IRS processes your refund and shows DDD on transcript, 2) SBTPG receives funds and updates to "funded" status (usually 1-2 days after DDD), and 3) SBTPG transfers to your bank account (another 1-2 days). The total timeline from transcript DDD to money in your account is typically 3-4 business days. For business planning purposes, I'd recommend budgeting for the longer end of that range to avoid cash flow issues. One tip: SBTPG usually updates their status overnight, so checking first thing in the morning tends to be more productive than checking throughout the day.

lmaooo irs really said log off and touch grass 💅

Been there! The lockout is super annoying but it's usually because the system is being extra sensitive. Make sure you're using the EXACT refund amount from line 35a of your 1040 (not what you think you'll get). Also try using a different browser or clearing your cache - sometimes that helps with the login issues.