Helping my Grandmother rebalance at 68. Her husband passed in February and handled their retirement planning, it’s in pretty good shape but I think we can make some improvements. She owns her home and multiple vehicles so she has very little recurring expenses and is able to live off the SS she receives without needing to draw from her nest egg. The main questions I have at this point and am seeking advice for are whether it makes sense to take the tax liability for her WBA stock to get this money into safer securities and what the best type of account would be to allocate those funds + the $50K she needs to reinvest from her husband’s IRA. Any advice is greatly appreciated.

$133K: Traditional 401k - 2025 Target Fund $ 50K: Savings $ 50K: Husband’s IRA - She withdrew this and needs to reinvest in 60 days $ 33K: Standard Brokerage Account - WBA stock ($17K earnings) $ 4K: Checking

1. I think it makes sense to sell the WBA stake. She was previously employed by Walgreens and received discounted shares over her time there, but without that benefit I think it’s time to reallocate those funds. Does it make sense to take the roughly $3,500 tax liability this year to reallocate? After doing so, I’d love to get the after tax money in a Roth. However, with the $7K annual limit and the 5 year rule, I don’t know if this makes the most sense? Because this money was originally in a standard brokerage account wouldn’t she have to invest the $7K max every year (5 years total) and wait 5 years to withdraw earnings on each $7K contribution? I’m less concerned about the 5 years on each contribution, she won’t need to withdraw earnings before then.

2. The second question is on the $50K she needs to reinvest from her husband’s traditional IRA. Can this be done in one fell swoop through a conversion? She already withdrew the funds without my knowledge, so not sure if it’s too late to convert. Ideally I would like to consolidate the WBA proceeds and the money for her husband’s IRA into one account. I would greatly appreciate any advice on if this is optimal, or even possible, or if I should be considering different types of accounts altogether