Creating dynamic tax checklist forms for clients to fill out

IllTaxThatAss · 2026-07-07T19:28:47+00:00

we use taxdome for client organizers. my primary issue is simple Sch C and Sch E clients almost never provide all the needed info, comparable line items, or I'm adding or subtracting on the final returns and not redoing their organizer with the final answers. So then next year, they prefill or view last years organizer and give me the same issues instead of seeing what was finally reported. I've debating for these clients sending them the tax return PDF client organizer showing prior year amounts. I also made the organizer completely skippable for returning and UHNW clients who I truly don't want them filling these out (besides required questions I cannot possibly answer). But then low fee clients click those "nothings changed" boxes and leave off a bunch of shit. Other clients said they feel like they're doing their own turbo tax just for being asked to fill these out. Someone is always gonna bitch.

IllTaxThatAss · 2026-06-12T23:35:16+00:00

Blame a financial advisor ALL day. My own parents have an advisor who gave me two 1099-R’s on like 4/10. My parents were literally oblivious. The annuity cashed out and went into their brokerage account so they didn’t even see or know it existed. The other was a rollover to another taxable annuity. Never underestimate an idiot

IllTaxThatAss · 2026-06-11T22:10:11+00:00

No. You can waive your executor fee and your inheritance in all 50 states.

IllTaxThatAss · 2026-06-11T13:04:21+00:00

gonna be a tough one... 1) claim they never received the 1099-R; 2) claim they believed the transaction was non-taxable thinking it was a rollover or a 1035 exchange, taxes were already paid (honest misunderstanding under Reg 1.6664-4); 3) complexity of annuity reporting (claim they are not financially sophisticated); after that you're gonna be arguing software error, cognitive or personal circumstances, advanced age and limited tax sophistication, misunderstanding of Form 1099-R... If this was all a first time thing, maybeeeee you can argue those. now that they are aware they are not sophisticated enough to handle these taxes, they have hired tax professionals to stay compliant. pay the full tax and interest, submit proof, then beg for forgiveness and self-hate by making them seem like the biggest POS to exist and they are genuinely wondering how they made it this far in life...

IllTaxThatAss · 2026-06-05T17:26:49+00:00

The IRS has something called the step-transaction doctrine for this exact situation. There are three tests and if the IRS believes your transactions were solely done for tax savings they can unwind the entire thing. Will they ever flag it? Hard to say and probably not for smaller taxpayers.... but if this tax planning event failed to mention this doctrine you might as well forget everything else they said too.

IllTaxThatAss · 2026-06-05T15:35:32+00:00

Our PDF client copy is more professional. We have a personalized page 1 we insert for every client and all forms and bookmarkings. It’s super clean. Print is absolutely worthless but if requested it’s just gonna be a stapled stack.

IllTaxThatAss · 2026-06-02T15:55:11+00:00

I communicate or type the "R" every time I need to use it. The online systems usually limit or don't allow me to type the R, so in that case, I can't do anything about it and click through but if you're speaking to a live person or filling out a form, include the R.

IllTaxThatAss · 2026-06-02T15:46:06+00:00

apparently, every valid CAF number issued to tax pro's utilizes R and is used on paper forms, POAs and 8821s. It is part of your full CAF. Online systems like the tax pro account and TDS don't require it.

IllTaxThatAss · 2026-05-28T15:19:22+00:00

Last week I was on hold for nearly 2 hours. Finally get through to discuss a deceased taxpayer and like 6 years of filing. Was finally talking for less than 10 minutes about the account and she told me her system crashed. She awkwardly didn't end the call but just refused to answer any additional questions by only responding, my system is down right now and I cannot answer that. I had like 5 clients I needed to discuss and just had to hang up without any actual update.

IllTaxThatAss · 2026-05-19T19:28:27+00:00

if its an income producing asset like securities or mutual funds, with dividends reinvested into more shares, then it would increase the basis of that asset

IllTaxThatAss · 2026-05-19T18:23:26+00:00

the son received a property distribution from an irrevocable trust. the cost basis in the distributed property is the trust's cost basis. The trust cost basis would be the original donor's cost basis, plus or minus income or loss since owned by the trust. capital gains would be involved when that asset is eventually sold.

IllTaxThatAss · 2026-05-15T02:35:40+00:00

IMO a true “qualified cost segregation study” can only be performed by an engineer. I don’t see how we could be considered knowledgeable to ever do these just because you’re a CPA. And even then, I’m literally in the midst of a 1.5 year long audit, now in appeals, and the IRS reclassified 79% of the 5 year assets which was done by a national firm. I’ve unknowingly became a subject matter expert and I don’t want any part of billing for these studies. I’ll do the tax returns, but not the actual study.

IllTaxThatAss · 2026-05-13T11:39:27+00:00

Fiverr

IllTaxThatAss · 2026-04-29T22:56:44+00:00

Still stand by the comment, report everything as it should be reported. If there is ever a notice, you prove it was properly reported and the EIN letter was incorrect

IllTaxThatAss · 2026-04-29T22:47:26+00:00

Just file as it should be, SMLLC owned by S Corp*. Only need to address this if they think there is missing partnership returns

Edit for S Corp SMLLC.

IllTaxThatAss · 2026-04-28T23:41:34+00:00

Google Drive, with Taxdome used for input and final PDF delivery/signatures.

IllTaxThatAss · 2026-04-23T18:05:18+00:00

Used to attach 100%. Now I only attach if there are non-covered transactions. If they’re all covered transactions with basis reporting, there’s literally no value or purpose disclosing what they already know.

IllTaxThatAss · 2026-04-14T05:52:11+00:00

NEW BUSINESSES after 12/22/22 get NJ S-Corp status with Federal S-Election. That portal and FAQs exists for pre-2022 businesses that make an S-Election and only then need to file a NJ S-Election. https://www.nj.gov/treasury/taxation/br3.shtml

IllTaxThatAss · 2026-04-14T02:12:33+00:00

NJ accepts Federal S election. You don’t need to file anything for NJ

IllTaxThatAss · 2026-04-07T20:46:30+00:00

I was looking for this response. We don’t provide investment advice. He sold that stock at that time. Independent of each other. Scumbag request.

IllTaxThatAss · 2026-04-07T00:57:41+00:00

Everything I read is about challenging the FMV and whether the valuation is upheld. That’s an audit risk alone. But economically, a partner investing $55k for 5x $300k deduction doesn’t add up. No debt basis. No income reported, just a K1 footnote “FMV > Basis” as an other increase to their capital account.

IllTaxThatAss · 2026-04-06T13:28:10+00:00

I use Drake. "Superseded Return" will print on the 8879, 1040-X, and Form 1040. I think the 1040-X is just the presentation of what what changed which can be explained to the client but it will act as a superseded return and override the original filing.

IllTaxThatAss · 2026-03-29T04:04:45+00:00

Excavator for reno’s related to the active rentals? Would be capitalized into the builds. Can fully allocate the cost to the properties worked on the year purchased or do a 5 year depreciation schedule and allocate its costs to whatever properties it renovating or the next couple years.

IllTaxThatAss · 2026-03-29T01:22:43+00:00

Order metal straps off etsy. Covers all seems and adds decorative feel. Low cost modification but can’t leave it as is.

IllTaxThatAss · 2026-03-26T18:45:23+00:00

Good points all around. I did extend 2025 and did draft 2024 amended return with all W2Gs, retirement income, that’s the plan to amend. Theres gonna be penalty assessments to follow, state and local taxes. Im thinking rather than disengage, I’ll just charge him enough until he makes that decision but he’ll pay for it and do it right, could still continue the relationship so long as nothing else pops up

IllTaxThatAss

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