Retaining back up documents - Roth IRA conversion and also Medical docs

Twelve or so years ago, I had to amend my Federal Return due to an accountant incorrectly calculating conversion to Roth IRA's for both my spouse and myself. The amended return was accepted We have not taken any RMD due to our age, but am wondering if I can now get rid of all the paperwork (except for the returns). I'm referencing paperwork and correspondence back to the original 2004 IRA contributions including several changes of companies that managed the IRA's before and after conversion.

Y'all are probably laughing at me, but I worked in the legal field and was taught to NEVER throw anything away!

2nd question - do I need to keep all the supporting docs for years worth of medical expenses? I don't believe I ever was able to itemize them, but kept for HSA backup.

Many thanks!