**This is NOT a sponsored post.**

I actually have no real issue with taxes as a concept. I drive on roads, so I want them to not be pothole death traps. Even though I don’t know if kids are ever on my agenda, someday the children of today will grow up and be my coworkers and our future president and I prefer they not be uneducated fools. Even programs like welfare; some people actually do need it (way to fail, Church… but that’s an entirely different rant), so I’m ok with supporting it.

What really gets my goat is the complexity of taxes. If you’re one of those people out there saying that taxes aren’t that hard and are doing your own, I still wonder, how many hours of research did it first take for you to become that capable? Because honestly, if the government wants to take my money, I don’t think they should make it that complicated.

Partially, I suspect this is psychological warfare on their part. Bear with me. Just using myself as an example – I consider myself pretty well educated. I regularly pick up new skills on the fly at work. I can even program a VCR (on the incredibly rare occasion I come across one these days).

I cannot figure out taxes. Especially if they get more complicated than one or two W-2s.

Because of this, I don’t hesitate shelling out money for tax software or preparers. Nor do thousands of Americans. And while its all fine and dandy to tell me that cost can be deducted next year, that’s only useful if I itemize.

Roughly only 30%* of Americans itemize.

I also feel this insane tax setup funds a ton of jobs in the government (therefore increasing the quantity of cash I’m forking over). If you were just looking for people who flat out didn’t file their taxes vs. wading through that soul-sucking pit of paperwork to make sure they were done right, that would take a lot less people.

Sigh.

Personally, this year was particularly rough. The last several years, I’ve used TurboTax and been pretty happy with it. I feel it does a great job with simplifying your taxes. The problem is that it gets expensive after a certain point if you’re filing multiple states and it struggles with NY (if you’ve worked in multiple states) because they do their W-2s a little differently. It also caps the number of state returns you can do. For most people, this is not an issue.

Additionally, a good friend who used it for a few years went to try to get a mortgage and found that retrieving previous years tax information was difficult and didn’t print papers with the same numbers as what he filed. It actually held him up getting the mortgage and almost lost him the property overall.

With that in mind, if I knew I had a big purchase coming up, I would probably not recommend using TurboTax. In all fairness, I haven’t heard anything like that from anyone else – but I actually watched him struggle through that whole nightmare, so it’s not secondhand knowledge… well, for you it is.

All that being said, most of you will never work for the circus or out on a tour, so you’re unlikely to ever have 18 states W-2s show up on your doorstep and make you hate life.

This year, after hemming and hawing, winding up with TurboTax telling me I made over $80,000 (seriously, where? Make it rain, TurboTax) and then pitching a very childlike hissy fit over what was going on, I went to H&R Block. For me, the final straw in that decisions was that at least if this all gets jacked up, someone will have my back in the audit.

To begin with, my tax preparer didn’t instill much confidence in me that she knew what she was doing when it came to the pile of W-2s I dropped on her desk. An hour and a half later, $120 poorer, I walked out with my federal, New Jersey and New York taxes done. Federal cost $40 and New York and New Jersey cost $40 each. Ugh. I didn’t even get that much back from New York. And I owed $61 to the federal government. We talked about the rest of my states, but it was $80 each to file them. And, on average, I was getting about $3-8 from each of them. Sigh.

I then went home and did 4 more states on TurboTax. Because their price was only $15 a state – MUCH better – coming out to an additional $45. So overall, I wound up paying $180 to pay $61 more.

In return, I got $35 from South Carolina, $47 from Virginia, $27 from Kentucky, $29 from New York, $79 from New Jersey, and $80 from California all to the tune of $297. So I kept a whopping $117.

$61 of that went to pay my federal taxes. So yeah. $56 dollars this year. Totally worth the 6ish hours it took to get my taxes done between H&R Block and TurboTax. My own money back, at twice the amount of work and headaches it took to earn the money in the first place.

I wound up leaving about $100 on the table because I had no idea how to file all those other tax returns for the other states and no desire to figure out how and put in a bunch of hours over $3-5.

Honestly, I wasn’t impressed with H&R Block and will not be returning. Unless I just really want the audit protection. But I feel like having watched the process beginning to end now, I can more confidently navigate it myself, should it happen again in the future. Plus, I’m sure I can find a free tax calculator or something similar online.

Hopefully my future never includes 18 states of W-2s again though.

*I didn’t just pull this number out of my behind. I read through several pages on Google and amassed an average of the last few years.