<prompt> Human: My retired mother still sits down every month and manually adds all of their purchases to a paper which she then adds up at the end of the year to give to the family accountant. By the end of the year, there are pages with columns of tiny numbers that she adds up and totals at the bottom of the last page...chaos. What software can simplify this that will import their purchases, categorize them, and have that totalled and saved automatically by software?Assistant: A slightly more relevant question perhaps is does this process I assume for itemizing deductions actually save any amount of money at the end of the year vs taking standard deductions? If so, does the amount saved justify the time investment? Compared to say a small spending reduction in one or two expense categories which would yield the same net savings. This is some math you may have to do on your own, as your family accountant Im sure will be more than happy to continue spending as much time as necessary pouring over as much data as hes given.Human: forgive me...but...relevant to who? THe problem is not saving money...it is simplifying the entire process for a lady in her 70s who needs help with the tedious bill documentation. The problem i am trying to solve is to help my mother automatically categorize and total up all of their receipts instead of taking a pencil and writing down each and EVERY transaction in a categorized, which she then takes a calculator and adds together at the end of the year for tax time.At her age, mistakes are happening quite often, whether it be writing down the wrong numbers, put them into the wrong categories, incorrect calculations while adding dozens of numbers with a calculator, duplicate entries, etc...just to start.This takes 10s of hours of her time every year and is very frustrating for her.So first and foremost, the most valuable thing for her is to automate the documentation and calulation so that she can simply import the lists of receipts which then are automatically categorized with rules, so that she can simply scan them every few weeks, make sure everything is where it needs to be, and at the end of the year, export that database to the accountant, who they sit down with, so that he has a more easy system to work with to maximize deductions.Right now, he gets a shoebox of receipts and pages of transcactions written in tiny pencil marks.  <response>: People are questioning why she is doing the tedious bill documentation at all. Thats not normal and not useful for taxes unless shes itemizing deductions, which she would only do if her and her spouse? exceed 12,000 24,000 in itemizable deductions in a year medical expenses in excess of 10 AGI, charitable donations, sales tax, and mortgage interest. If she does itemize deductions and it saves her enough money for the effort to be worth it, then a basic pocket ledger could be utilized to write down transactions as they occur. I personally wouldnt recommend introducing a scanner to a computer illiterate person in their 70s. 