Writing Off Train Travel at Tax Time Can Be Tricky.

I’ve been working on our taxes over the past several days. It’s an awful job. I don’t understand most of it, my records aren’t the best, and I have a problem staying focused. It always takes a great deal longer than it should.

I’m on the board of the National Association of Railroad Passengers and, because it’s a registered non-profit organization, the money I spend traveling to and from the semi-annual meetings is deductible. I fly to the west coast, of course, but take Amtrak from there to wherever the meetings are.

That’s where a lot of the time goes compiling my travel expenses to and from the NARP meetings. The problem is, I usually take side trips before or after the meetings and that confuses things. After our April meetings this year, for instance, I’m going up to Boston for three days to meet some family and to see the Red Sox play. So, clearly, thosetravel costs shouldn’t be claimed as deductions.

That’s when I start to seriously over-think things usually in the wee hours when logic and clear thinking have fled the scene. Here’s how my thought processes were going off the rails last night:

If I weren’t going to Boston, I would be taking the Capitol Limited from Washington back to Chicago. The cost of a roomette for that trip is $317. But I am going to Boston, so I’ll be traveling to Chicago on the Lake Shore Limited and — uh-oh! — the roomette on that train costs $589. So can I get away with deducting the larger amount? It’s not really fair to the IRS.

But wait a damn minute!. Most of the time I use my airline miles to get from Hawaii to the West Coast. I had to pay out dollars and buy stuff to get all those miles, but the IRS won’t let me deduct those miles and that’s not really fair to me!

See what I mean? That’s pathetic! Eventually, rational thought ceased altogether, and I went to bed.

This morning, along with the sun, came illumination, bringing with it a simple solution: I’ll stuff everything into an envelope and FedEx it over to Michael More in Honolulu. He’s done my tax returns for 30 years and is meticulous down to the smallest detail. If I should get a call from the IRS, I’ll be incredulous, then I’ll be indignant, and then I’ll blame Mike.