dsmexpat, that was the git of much of that list: it's hard to figure out how to do things, so might as well work another two decades so you don't have to do them.
Dude, if you can't figure out how to rollover your 401K into an IRA to get the Roth ladder started in 20 (!) years, or hire someone to figure it out for you, I'm a little scared how you got your medical qualifications...