Thank you all for the advice and suggestions. I am busily at work simplifying my portfolio along the lines suggested.
For starters, I'm paring down the number of funds within the 401K's. It's just taking a couple of days for the BrokerageLink funds to settle back into the base account. Once that completes, I can then do partial rollovers for the last bit of after-tax source money. I can then move on to streamlining the IRA's.
I really like the idea of rolling both 401K's into a single IRA before I hit RMD age, but I'm not quite ready to do that. I like the Net benefits Interface and I like the low expenses ratios in my 401K plans, and I have a few years before RMD's apply. I think what I might do is convert just one of my 401K's into an IRA now. That will reduce overlap and complexity. Moreover importantly, it will be very easy to roll the second 401K once the IRA structure is all set up.
I do have a follow-on question to the recommendation posed by @HomeStretch regarding spending down the HSA. I am older than 65 and I have been saving medical receipts for ten years. Consequently, I can withdraw a good bit of my HSA right now on a tax-free basis. My question is how best to use that HSA money to fund Roth conversions. Should I pull just enough out of the HSA to cover just the taxes on a Roth conversion or should I withdraw a larger amount so that I don't have to withdraw as much from a 401K for living expenses? That would allow more headroom to do a larger Roth conversion. I know taxes and marginal rates are pertinent; I'm just trying to wrap my head around the general strategy.
For starters, I'm paring down the number of funds within the 401K's. It's just taking a couple of days for the BrokerageLink funds to settle back into the base account. Once that completes, I can then do partial rollovers for the last bit of after-tax source money. I can then move on to streamlining the IRA's.
I really like the idea of rolling both 401K's into a single IRA before I hit RMD age, but I'm not quite ready to do that. I like the Net benefits Interface and I like the low expenses ratios in my 401K plans, and I have a few years before RMD's apply. I think what I might do is convert just one of my 401K's into an IRA now. That will reduce overlap and complexity. Moreover importantly, it will be very easy to roll the second 401K once the IRA structure is all set up.
I do have a follow-on question to the recommendation posed by @HomeStretch regarding spending down the HSA. I am older than 65 and I have been saving medical receipts for ten years. Consequently, I can withdraw a good bit of my HSA right now on a tax-free basis. My question is how best to use that HSA money to fund Roth conversions. Should I pull just enough out of the HSA to cover just the taxes on a Roth conversion or should I withdraw a larger amount so that I don't have to withdraw as much from a 401K for living expenses? That would allow more headroom to do a larger Roth conversion. I know taxes and marginal rates are pertinent; I'm just trying to wrap my head around the general strategy.
Statistics: Posted by silasmarner — Tue Oct 21, 2025 8:11 pm — Replies 7 — Views 1143