u/Sophie_Bella

Just found out that boldin does not recognize the fact that PA does not tax IRA withdraws (or conversions). This seems to me to be a pretty big bug that can multiple over the years on the withdraws from our Traditional IRAs. I am a very big proponent of Boldin - but this has dampened my faith in it greatly as to me, this is a key issue. Now, maybe the AI is wrong? I hope so, but if that's the case, how does it get something so straightforward wrong.

https://preview.redd.it/iatbg63st4jh1.png?width=866&format=png&auto=webp&s=adb74bf0124294e8d02c1010072710bed4825fde

I used the Roth Conversion Explorer and selected the option to stay within the 22% federal bracket. The Explorer created a conversion of $263,464 for 2029. However, when I look at the actual forecast for that year in boldin, total taxable income lands at $243,488 (today's dollars), with $34,596 of it falling into the 24% bracket — not the 22% bracket I selected.

I dug into the year-by-year numbers and found the cause: in 2029, my plan also shows a separate, forced withdrawal of $34,998 from the same IRA triggered because my other cash and taxable accounts are depleted by that point in the plan. This withdrawal is not part of the Roth conversion — it's the withdrawal-order engine pulling from the same account to cover spending — but it adds ordinary taxable income in the same year, which is what actually pushes me over the 22% line.

The in-app AI assistant confirmed the mechanism: This is the AI's actual response: "The honest answer is that the Roth Conversion Explorer and the full forecast engine are separate systems. The Explorer runs a simplified optimization that doesn't loop back through the withdrawal-order engine to check whether its own conversion will create a shortfall that then generates more taxable income. It's a known limitation — it solves for the bracket in isolation, not in a closed loop."

It might be a known limitation, but if that is so, the tool should at least warn us or present some time of info when you run the explorer by tax bracket. In this situation, it should have reduced the suggested roth conversion by the overage keeping me in the 22% tax bracket. Am I wrong to expect that behavior of the roth explorer? Now, if the AI would have told me that they applied inflation to the tax brackets, or they applied standard deductions then it would have made sense to me, but it didn't tell me that. It told me that the roth explorer and the plan are two different systems. I think the roth explorer is one of the areas, if not the main areas, that needs the most work in the tool.

I asked the AI to open a support ticket.

I think one of the biggest variables that is overlooked in financial planning is what numbers are you using for your longevity numbers. Financial planners tend to want to use 95 for both or sometimes 90 for the male 95 for the female. But everybody's different. Anyway it's a big variable and so I wanted to make sure I wasn't being too conservative by having our longevity numbers too high. So I use Claude. I asked it to create me a questionnaire of all the things they would need to know to calculate our longevity ages. Things like our current lifestyle and information about our parents and sisters and brothers and aunts and uncles in terms of when they died and from what. List of medications were taking list of supplements were taking, etc. after filling that out and uploading it to Claude in addition to our quest lab reports for each of us it came back with a very nice report that showed a conservative age of most likely age and an optimistic age. Included all of the items that are working in our favor and also all the items that are working against us. So what I did is for my baseline I used the most likely numbers. Then to stress test that I created a scenario with the optimistic numbers. And then compare the scenarios, some very interesting results. Living longer lowered the chance of success which one might expect, but living longer also left us more at the end of the plan. When inquiring about this, we have more money at the end of the plan because we have more years of collecting Social security, and since I'm not going to collect Social security, either of us, until age 70, we're well beyond the break-even point in the long longevity scenario. But the reason the chance of success goes down even though value and plan goes up, as Claude explained it, is that it's five more years that the Monte Carlo simulations are using which means five more years of potential downturns in the market.

Just thought I would share this in case anyone else was interested in giving it a try. I feel I have a better, more realistic plan, of course no one knows when our time will come, so the best we can do is take our best guess based on data.