Based upon my most recent health situation (but still planning on another 20 years) I finally decided to do something that I've been putting off for over a decade: simplifying our finances.
I spent about 4 hours every day for the past six days cleaning up and moving money around in a very messy, complicated set of checking, savings and investment holdings. Didn't sell anything mind you, but we just had money placed, invested, coming in and going out from way too many different avenues.
Before ER it made sense but things have settled down and we need something much, much cleaner so that DW can deal with it in the event I'm not able to help. "Why are the lease cars automatically paid out of savings account #3?" "I don't know, why do we even have three different savings accounts?." Three checking accounts? One credit card who's only job is to pay the cellphone bill? Some dividends go to one account, others to another, outside income to a third?
Automation of the above facilitates such nonsense as you never have to think about it, but it's incredibly cumbersome when you have to figure out what's going on.
Then I also cleaned up my disabled brother's accounts that were equally and needlessly complicated. IRAs all over the place, income coming from all kinds of places.
Still need a few more hours and then a lot of monitoring to make sure everything is going where it's supposed to, but a very satisfying and worthwhile endeavor!