as far as tax organization... at some point, you might suggest that he go talk to a .. erm... financial planner/advisor/counsellor/whatever they are called, for better ideas on how to organize himself, in a style that fits him best
The lady that use to do our taxes tried everyway in the world to work with him, but he would not cooperate. He is not disciplined to do any of that paperwork or anthing he needs to do. I even offered to be his secretary and keep his bookwork if he would just bring in the recipts, I would take care of everything. He never did. When he got into his old truck after buying something to paint with, he would throw the receipt up on the dash and it would lay there until the sun would fade it out. He has his truck so junked and trashed until I just want to die when people see it.
So, I am at my wits end with him. He is not motivated to do much of anything. It's not that he is just downright lazy (at least, I don't want to think he is), but he is slow moving and it takes him a long time to get moving. He is not disciplined about much of anything. Once he gets to working, he works hard. But, my patience runs out real quick. I've learned not to say anything b/c it doesn't do any good and just causes hard feelings. He is very different from me.
It is not about what you feel should work in your M. It is about doing the work that gets the right results. Do what works!