Tax Time: Soldier Through Alone or Get Help?

Every March I sort through my prior year’s financial history, add the profits and subtract the losses, enter the numbers in a booklet provided by my tax accountant, place all the corroborating evidence in plastic folders, and clip the folders to the appropriate pages.

 “Oh, the rest of my clients could take lessons,” my accountant gushes. “This is beautifully organized.” But for all my hard work, the only thing I seem to get back is gratitude. When it comes to the income tax returns themselves, we don’t, by mutual agreement, cheat, fudge, or even snicker. As for his fee, I don’t think my accountant really cares much whether my records are in a leather portfolio or jammed inside a pair of old tube socks. He charges the same -- a lot -- one way or the other.

I kind of resent paying the accountant so much money to simply transfer the arithmetic from my forms to his. I feel particularly resentful as he typically finishes early and we spend the rest of the hour discussing the progress of his vineyard in Napa.

So this year, rather than fork over my hard-earned pennies to learn more about the growth habit of the California pinot grape, I decide to take matters into my own hands. I’ll file my own taxes. When it comes to numbers, I’m not a half-wit. I’m not a full wit either; I fall solidly within the three-quarter wit range. Besides, and not to get too personal about this, I didn’t exactly win the lottery last year. My 2011 financial escapades make for some pretty dull reading.

When handling your own tax returns, the first decision is whether to e-file or paper-file. As I haven’t time for the e-file learning curve right now, I sharpen a pencil and plan to party like it’s 1999.

Using last year’s return as a template, I go in search of forms. Which, in spite of the Internet, turns out to be surprisingly difficult. Of course, making fun of any dot gov site is like shooting fish in a barrel, but the IRS site is particularly incoherent, sporting old-school links scattered all over one ugly home page.  Apparently I'm not the only one partying like it's 1999.

Some of the forms I need do not appear when I click on FORMS, and they still don’t appear when I click MORE forms. I try for some navigational advice by clicking TAX MAP, which turns out to be a map in name only, so then I move to the FAQ.

I hate FAQ’s, with their perky, disingenuously stupid pretense that we’re conversing in-person.  “Where can I …” and “Why do I …”  Spare me this antiquated attempt at warm and fuzzy, which couldn’t have fooled anyone even back in that party year of which the IRS and I are both so fond.

I find a link for FORMS AND PUBLICATIONS, and that takes us back to where we started. Time to try this from another angle: If I were a Schedule E and didn’t want to be found, where would I hide?

This line of thinking does the trick. I locate 82 pages of IRS publications and forms, with 25 listings per page.

Wow. Consider the possibilities. I mean, call me naïve, but are there really 2,000 distinctly different ways to explain how we got and spent money? I can’t even come up with ten.

Eventually I find Schedule E --well, the instructions for Schedule E, anyway.  It seems a shame that when it comes to a clearly disastrous investment of less than a $1,000 such as mine, there’s no Schedule WTF.

I wade through eight pages of rules and regulations, and just when I’m ready to talk myself into chucking the E and everything it stands for, I see a Tip. Or is it a Caution? The IRS publications litter Tips and Cautions all over the place, which they should really group under a general heading of Or Else. I suggest adding this to the Q&A:

Q:  What happens if I fail to properly file Schedule E?

A: We’ll put you in a chokehold from which you’ll never recover.  

Ok, my right eye is beginning to twitch, and I haven’t even started to look for Schedule M. Or printed my first and last name on anything, for that matter.

Nor will I. The reason I’m not now nor will ever find the other forms and schedules, with attendant worksheets XXX.88R to be filled out once the XXX.23S is completed in the event XXX.24T proved requisite, and see page XXXC, line 8X if you have questions, is because I’m busy making a call.

Who to? You do the math. The upside is, if you want to know anything about last year’s pinot noir harvest, call me next week.