TAX TIME! – And The Role of Virtual Machines

It’s 2014 and we all know what that means:

  • Gym – 3 times a week.  You owe it to yourself, gurrrrrl.
  • Post christmas shopping blowout sales on all bedazzled underthings.
  • And taxes.  Taxes.  TAXES!  TIME TO START ON YOUR 2013 TAX RETURN!

I will proudly squeeze body into a bikini this summer and my underthings don’t need any extra bedazzling.  But my taxes need to be done on time and in order.

TurbTax and TaxCut and other similar products (that I’m not familiar with) have been around for quite a while and can do a very nice job helping most people through the details of their return.

Personally, I have been using TaxCut for about 5 years because it’s usually a little cheaper than TurboTax, and changing products makes it difficult to import return from the previous year.  TurboTax and TaxCut both over “online” filing where you don’t need to install any software, but I’m also not familiar with these tools as I don’t fully trust that they won’t dump all of the information, that I spent 3 hours entering, right into the trash heap.

For a few years now, I’ve been using Virtual Machines to help facilitate this annual number crunching drudgery.

For those that a bit less “tech savvy”, virtual machines are basically fake computers inside your real computer.  Each year, I clone (copy) the previous year’s virtual machine and install new software on it for the new tax return.  Also, I’m going to say “VM” in place of Virtual Machine from now on even though both sound terribly pretentious.

I have two very important reasons for doing this:

  1. I don’t like the crap most tax software installs on my real computer.
  2. Each clone is a pristine image of that years tax filing process.

For the VM software, I use VirtualBox because it’s free, runs on many Operating Systems (Mac/Windows/Linux), and uses some pretty standard disk image formats.

My real computer is a Mac (OS X), but the TaxCut software only runs on Windows.  But even if it could run on my Mac, because of #1 above, I wouldn’t want to install it there.  Installing Windows is not terribly hard, but you’ll need an install CD or an .iso image.  How to go about purchasing a copy of Windows is a story I don’t want to tell as it pains me greatly.

After installing windows, the very first thing that I install (after waiting 62 hours for updates to complete) is PDFCreator.  PDFCreator allows you to create .pdf files from any application that can print (and they all can).  This is super important because you will likely be asked to physically print your returns many times over.  I always print them to pdf files and save those away in a nice safe, backed up place.1

My VirtualBox installation currently looks like this:

Screen Shot 2014-01-01 at 2.08.33 PM

Four VMs.  All running Windows 7.  I have more from previous years, but changed software and deleted them because their usefulness grew thin.

Each VM has been cloned from the previous year, starting with “Taxes 2010”.  After cloning, I go ahead and install the current year’s software, which I don’t have just yet for 2013, so I can’t show it to you.  But the end result is that “Taxes 2012” VM (for example) will have TaxCut software for 2010,2011, and 2012.  Like so:

Screen Shot 2014-01-01 at 2.13.08 PM

VirtualBox provides a nice way to share files between the “real” computer and the virtual one, so it’s easy to get your saved returns onto your computer when finished.  You should be doing this as well as printing/saving a pdf file.  And if you have no digital backups, definitely print a paper copy and stash it away.

I like the way this has been working for me so far.  In the future, I may need to switch to Windows 8 or something else, but the TaxCut files can easily be copied over and imported to the next version so I won’t need to re-answer all those silly questions again.  And, for as long as I may need them, the previous years’ VMs will be available for reference.

Godspeed, tax filers!

  1. I’m almost certain that TaxCut now has a “Save to pdf…” button that makes this step moot.  But it’s still handy to have just in case you need to save receipts from web sites and what not. []