Man I suck at taxes! Question about filing late 8606 ...

Ok, so, I have a bit of a complex question on filing late 8606's. 

 

Some quick background. Back in 2018 and part of 2019, I contributed to a ROTH and didn't realize I was above the income limit. In 2019 (after filing my 2018 taxes on time), I realized this and recharacterized both 2018 and 2019 contributions (then continued contribution to the TIRA for the remainder of 2019). I amended my 2018 return to include form 8606 (there was no electronic filing so had to mail in the amended return).  Then, like a true idiot, when I filed my 2019 taxes, I didn't include form 8606. Finally, the pièce de résistance -- with the most recent 2023 filing, I did include form 8606 but only the contribution for that year and not a rolling basis of all prior years. Don't ask me why or how this happened -- I'm just that awesome. So to recap:

 

2018 - filed 8606 with $5.5K basis, no deductions taken (recharacterized ROTH to TIRA via amended return)

2019 - no 8606 with $6K basis, no deductions taken (recharacterized but for same year contribution before filing taxes)

2020 - no 8606 with $6K basis, no deductions taken

2021 - no 8606 with $6K basis, no deductions taken

2022 - no 8606 with $6.5K basis, no deductions taken

2023 - filed 8606 with $6.5K basis, no deductions taken (not rolling)

 

Here are my questions:

1. Can I just update the rolling basis when I file my 2024 taxes? Or do I need to file form 8606 (using the one from the respective filing years) for 2019 - 2022?

2. If I need to file each individual year, do I need to re-file form 8606 for the 2023 tax year to reflect the correct rolling basis?

3. Any suggestions on how I can wordsmith my lack of knowledge as reasonable cause? 

 

How awesome am I? This sent me down another rabbit hole of the benefits of a TIRA and now understand there isn't one unless you do a backdoor ROTH. But, oh the tax implications ... why didn't I just do it sooner ... this is going to be my next question 🙂

 

Thanks in advance for your help!