Tackling taxes Acrobatically (and paperlessly)

Search results from an Acrobat PDF Portfolio

Search results from an Acrobat PDF Portfolio

This marks the third year we have done our taxes via p2, our personal paperless workflow, using PDF and so far, Murphy preserve us, we haven’t had a problem. Not only do I scan in every receipt and other relevant paper document that comes my way, but all of my bank and credit card statements now arrive as PDF, via electronic delivery options at Wells Fargo, Chase, Amex et al. (this has cut down the scanning considerably).

The big drudge job around here, as in many households, has always been  dredging through statements picking out the allowable deductible items in 12 monthly bank statements, 12 monthly credit card statements  etc. We used to pore over the paper statements with a highlighter and a calculator adding up the bits and pieces.

More recently we pore through PDFs and do a search on vendor names (e.g. ‘comcast’).  For one set of figures, I search each statement for five or six likely suspects, multiplied by 36 or 48 statements.  Just opening that many files is work enough much less repeatedly searching each one for relevant data. In the past, I’ve used the Yep! PDF browser to fish the relevant documents from the sea of PDF on my hard drive – but still had to go mano a mano with each statement.

This year I tried an experiment: I dropped a couple of statements into the ‘portfolio’ feature of Adobe Acrobat 9, hoping that I would be able to do a global search on the bundled PDFs. In so doing, I discovered that Acrobat not only searches portfolios globally, but it reports search hits in a digest-like list that usually included the numbers I needed (see screenshot). Perfect! Five searches of a PDF portfolio with the amounts neatly returned beat the old way of performing 60 searches, five in each of 12 statements.

Of course, we’re dealing with software here, so it wasn’t that easy, due to what seems to be a bug in the Mac version of Acrobat 9. When I dropped bank statements into the Acrobat Portfolio window, the file names of 11 of the 12 PDFs were truncated to ’08.pdf.’ For some reason Acrobat would take 11 of the files, but rejected the 12th with an error stating there was already a file with that name.  Hmmm… looking at the files I saw they all were named, helpfully in this manner:

  • Statement 01/30/08.pdf
  • Statement 02/28/08.pdf
  • Statement 12/30/08.pdf

Apparently, Acrobat doesn’t like the legal Mac OS filename character “/” and was truncating all the characters before the last slash. I changed the offending file’s name (for some mysterious reason it was the June statement) to use dashes rather than slashes, and it went into portfolio just fine. So now all I had to do was get all the slashes out of any of my statement filenames, and we should be good to go.

Since I was already basking in the potential of computer automation, I decide to try to create an Automator process that would do the chore for me. Sure enough, after 15 minutes noodling in the Automator editor, I had a little applet (now named SlashToDash) that went through my entire directory of PDF statements and scans, doing away with slashes.

After that hiccup, all went as planned… I couldn’t believe how much easier this was than in previous years. Anyway, I next scanned in our tax man’s voluminous worksheets (he has an automated system won’t easily do PDFs), and used the Acrobat Typewriter tool to fill in all the relevant data  gleaned from the global searches. I then bundled his worksheets up with scans of the W2s, 1099s and other documents that had arrived in paper format, again, using Acrobat., and emailed him the whole thing.

My hard drive now has a Taxes 2008 folder that holds neat collections of all my statements, receipts, filled tax worksheets et al., together with scans of the stuff where I cheated and used paper. God forbid we should suffer an audit, but if it happens, we’re organized. Bring on the 2009 taxes… I’m ready…

The non-paperless approach to tax preparation

The non-paperless approach to tax preparation


2 Responses to Tackling taxes Acrobatically (and paperlessly)

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