u/Broly2912

Two weeks ago you helped me fix my Roth conversion tool. One comment stuck with me way more than the rest.

(for anyone who missed the first thread, it's here)

When I posted here last month I figured I'd get a few neat, thanks replies and that'd be it. Instead a bunch of you actually dug in, found bugs, caught numbers that were wrong, told me what was missing. I spent the last two weeks working through basically all of it. Full list below.

But there's one comment I keep coming back to. Somebody said, kind of joking, that they'd never bothered looking at the widow penalty because "of course my spouse will never die." And then added, but of course I should.

Honestly that's the whole reason this thing exists. The year one spouse passes, the one left behind isn't just dealing with that, the next year they're filing as single. Standard deduction drops. Brackets squeeze. The IRMAA tiers that were set for two people now hit one person at half the income. Same money coming in, thousands more going out in tax, at the worst possible moment to be dealing with it. Nobody plans for it because nobody wants to sit and think about it. That's exactly where people get blindsided, so that's the thing I most wanted the tool to make visible.

If you've got a spouse and you've never once looked at what their taxes turn into the year after, that's the thing I'd go model first. Takes two minutes and you don't need an account for it. Better to see it now, on a quiet morning with coffee, than to have your husband or wife find out the hard way when you're not around to help them through it.

Everything else below came from your comments on the last thread. Less heavy, but you asked for all of it, so:

  • Mixed ACA/Medicare households. One spouse on Medicare, other one still on ACA. Few of you flagged this. It's done right now, combined household income against the ACA cliff, separate IRMAA lookback for the Medicare spouse, both showing at the same time.
  • The IRMAA lookback. The thing a bunch of you kept saying, that your 2026 income sets your 2028 premiums and not the current tiers, that's front and center now instead of buried in a table. Projected years show as ranges with a note about when CMS actually locks it in.
  • Someone checked it against their actual SSA Medicare letter and the Part B / Part D surcharges didn't match. Fixed. Lines up with what SSA tells you now, Part D included.
  • The tax a conversion actually costs you. More than one of you pointed out the tax bill has to come from somewhere and it eats your headroom. There's a federal tax estimate now with the bracket by bracket math right there.
  • State income tax for CA, NY, NJ, IL and PA. NJ went first, because one guy wrote up this whole thing about how Senior Freeze and the NJ retirement exclusion stack on top of the federal cliffs. That comment straight up changed my roadmap.

Same as last time, free, and your income numbers never leave your browser, nothing gets sent to a server. Still no optimizer, still no "you should convert $X." It shows you the edge and the room you've got, you make the call. Every number opens up to show the actual IRS/CMS math behind it. The calculator itself needs no account. Couple of the extras (a forward RMD projection, and saving your scenarios across devices) sit behind a free signup, but everything from the last thread and everything I listed up there is open, no login.

Link: https://cliffedge.app

What I'd really like eyes on is the state tax stuff is the newest and least tested. If you're in one of those five states and a number looks off for your situation, that's the feedback I want most.

One last thing, since I know a few of you were tracking the 2028 IRMAA projections yourselves as the monthly CPI data drops (shoutout to whoever put me onto the Finance Buff updates). I keep the tables current as CMS and the CPI numbers land, and there's an optional signup if you'd rather just get a heads up when they move instead of checking it yourself. Totally optional, tool works fine without it.

To everyone who spent time on the last thread, genuinely, this is a better tool because of it. Thanks.

reddit.com
u/Broly2912 — 5 days ago

Built the Roth conversion cliff tool I was asking you about a couple weeks ago. Looking for people to poke holes in it.

Some of you might remember my thread asking how you actually land on your conversion number each year. The thing everyone said was basically the same, pick a MAGI ceiling, figure out the headroom, convert up to it, and don't trust tools that just spit out a recommendation.

I couldn't find anything that did just that cleanly, so I built it. Putting it here because you're the people who'll catch what's wrong with it.

It shows your headroom to seven cliffs (ACA, IRMAA, NIIT, the new OBBBA senior deduction, the SS tax torpedo, LTCG stacking, and a widow penalty simulator), gives you one max-safe-conversion number and tells you which cliff is the binding constraint. Every number has a toggle that shows the formula and the IRS/CMS source it came from. No optimizer, no hidden return assumptions. Federal only right now, state tax isn't modeled yet.

Free, no login. Here's the link: https://cliffedge.app

Few things I'd genuinely like to know:

  • If any number looks off, tell me which one. That's the part I care about most.
  • Does a single headroom number actually match how you think about this, or am I oversimplifying?
  • Most people I talked to live in Excel. Worth letting you import/export a spreadsheet, or would you rather just not deal with Excel if the tool's good enough?

Not selling anything right now. Just want to know if this is useful or if I've built something only I want.

reddit.com
u/Broly2912 — 21 days ago

Those of you managing Roth conversions in retirement what does your actual decision process look like?

Not looking for advice, genuinely trying to understand how people approach this.

For those of you who are already retired or within a few years of it and actively managing withdrawals and Roth conversions: how do you actually land on a number each year?

Specifically curious about:

  • Do you work backwards from a MAGI target (pick a threshold, calculate how much headroom you have) or forwards from your income (add everything up, see where you land)?
  • What's the hardest part of the decision? Is it the math, the uncertainty about future brackets, not knowing whether avoiding a cliff is even worth it long-term, something else?
  • What would have to be true for you to feel genuinely confident in your conversion number, not just "probably fine" but actually confident?
  • If you've built your own spreadsheet or tool for this, what made you build it instead of using something off the shelf?

Background on why I'm asking: I've been going deep on this problem space and keep running into the same pattern, people who are sophisticated enough to know the cliffs exist but still making the final decision somewhat on gut feel because nothing gives them the full picture. Trying to understand if that matches other people's experience or if I'm seeing a skewed sample.

reddit.com
u/Broly2912 — 24 days ago

Has anyone found a tool that shows exactly how close you are to an IRMAA or ACA cliff in real time?

I've been trying to model my Roth conversion strategy for the next few years and keep running into the same wall. Every tool I've tried (Boldin, Projection Lab, Pralana) optimizes for lifetime net worth or recommends a conversion amount, but none of them give me a simple visual answer to "how many dollars do I have left before I cross this threshold."

The IRMAA 2-year look-back makes this even harder because I'm essentially making decisions today that affect my Medicare premiums in 2027, and I can't find anything that maps that forward clearly without just trusting a black box number.

I ended up going back to a spreadsheet which feels ridiculous when I'm paying for software.

Is this a me problem or does everyone else just do this manually too?

reddit.com
u/Broly2912 — 1 month ago