On the question of paperless billing - Does anyone have any experience with handling financial affairs for someone who is no longer capable - how does that person having gone paperless effect the process ?
This is an excellent question. I think that Walt is on the right track. I don't have a good answer for anyone who has gone paperless, but I do have some experience with handling monies and bills for persons who were unable to do it themselves. It was about 15 years ago, and I got into the act a little late, trying to help some older people in our community, a man and a woman, who had lost spouses in the previous 6 months and while able to physically function fairly well, through depression and loss of interest, had not paid attention to bills of all kinds that had been piling up for months... bills, re-bills, threats, legal actions, eviction notices, utility shut offs and even older obligations from their deceased spouses... so double the trouble.
This is a literal nightmare. dozens, maybe hundreds of hours of letters, phone calls, and trying to bring some order to total chaos. Imagine five or six large paper bags full of bills, totally unsorted by person, type, amount, or date.
We are trying to head this off, without much success thus far. At the present, we are looking to keeping to paper bills as much as possible, and maintaining a virtual "spindle" type of sort... using "received by" and "paid" spindles (actually piles). Since we still have three properties, this seems to work out the easiest.
In an "after-the-fact" bill paying situation, the first step is doing a sort by date... without regard to type or source of bills. This allows for an easier elimination of duplicate bills... (especially important with medicare and all other healthcare bills).
Stacking/spindling/piling of bills allows for easier handling by a third party, where it's almost impossible to keep track of folders or even a spreadsheet-type of filing.
Back to the initial question... I can't see an easy way for a second party to pay bills on a paperless basis... particularly when it involves a different physical location (ie. mom's house).
Personal... in earlier days, I might have been able to keep this all sorted out, with some other system but as I look to the future, neither the interest nor the ability to do this. So not very clean or technical, but at least one standard method, that can be understood by anyone who might have to take over.
Best of luck on this... IMHO, a good question on a subject that will be important to all of us in time. Will watch for other ideas.