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After 3 years of retirement (and 37 years of W2s before that), I figured out that I may be able to deduct health insurance premiums. Check me on this please. I am fully retired but I am still on my old employers insurance plan as a retiree. I pay 100% of my premiums out of pocket. I can...

I'm interested in finding a good income optimization package. I retired in late 2019 and my original plan to tap various asset sources and my pension made a lot of sense in 2019 and 2020. Also, I started doing Roth conversions in 2021 and my best window for significant conversions is 2022-2024...

I recently had a thread about Roth conversions that describes my current situation/plan. BTW, I did a conversion in 2021 and will carry on as available. https://www.early-retirement.org/forums/f28/roth-conversion-thoughts-feedback-111091.html My current plan is to wait on my pension until...

Hi all. I’m interested in feedback, thoughts, resource recommendations or advice on how to think about planning for roth conversions in my situation. I apologize upfront for the length of this post but I have a bit of a different cash flow situation than normal so added some explanation. The...

My daughter is 24. She has accumulated a fairly sizable savings account and we are discussing her opening an investment account to put some money to work for the long term. She currently has a Roth IRA with about $8k and set up a monthly investment. (85% stock/15% FI) I have pointed her to a...

I retired in 2019 and some deferred comp was paid in 2020. They withheld about 80% of the Federal and State estimated taxes I calculated I will owe based on my expected 2020 income. Can I wait until later this year in 3Q or 4Q to make the remaining tax payments or do I need to do as soon as...

I’ve read the rules about early access with no penalty and just looking for more verification. I’m 56 and retiring after 25+ years with the same company. All my 401k money is in the companies plan. I can leave it there and access periodically if I wish until I’m 70. I understand I can w/d...

My pension has a fixed 1% COLA starting at age 66. I don't see away to model this in firecalc. Thoughts? Thanks, Dave

I've been reading this board for a couple years and found lots of helpful information. I've been working with an FA for about 5 years and think I will fully takeover management by this time next year. He's been helpful in planning and evaluating what we've been doing for a long time and...

I'm retiring at age 57. I intend to wait until 67 to take SS. I have over 35 years of earnings. Is the retirement benefit estimate on ssa.gov for FRA locked in or is it affected by my no longer contributing between age 57 and 67? Thanks, Dave