Adam, I never was more stressed than income tax time, and I too had the best books I could ever imagine. That is a stressor I am thrilled to not deal with anymore (from a business point of view). I have been retired 4 years, maybe 5 (actually I work as hard at this as I did working and being a good Pops). Anyways, I cannot wait for 7 years to pass so the stress of past book keeping finally ends. So a new tax policy would surely be nice. Just think of the man hours wasted trying to figure out an extremely complex system that even the IRS cannot understand. Amazing to consider is that you can call the IRS about an issue, get their expert opinion, and still have done your taxes wrong. The IRS gave you bogus information and you are still responsible and libel for interest and penalties even though you received your information from the IRS!? Crazy.
I believe I read that H&R Block sent out the same tax return to 100 accountants and received 100 different results!! YES!, this is one complicated beast even if half true.
All sales should be taxed, every transaction. Capture the underground economy by taxing sales of every item, and in doing this the system becomes clearly fair. Maximum taxes collected across the broad economy. That sounds good to me. Have no loop holes, just pay as you go.
I understand that any tax would become way more complicated than wished for but "keep it simple stupid" is still a great and fair motto to attempt. It won't happen though because we would have to lay a lot of IRS people off, and we don't do that.
Happy Voting
BOB

It's November, and, absurdly, I have *almost* put the 2011 tax season behind me.
Chris and I run a relatively simple partnership, but I have easily spent more than a hundred hours over the past year and a half with lawyers and accountants figuring out how best to structure our organization and account for everything cleanly and legally.
Then there are the hundreds of hours I've spent during that time building the monthly books, working with our bookkeeper to make sure they're accurate, and then working with the accountant to prepare estimated and final tax returns.
We've racked up many thousands of dollars in fees while doing this. And mind you, we're not trying to set up some crazy, convoluted, offshore or otherwise murky structure to evade taxes. Quite the opposite: We're trying to be as transparent and squeaky clean as possible (so that the chance of being audited doesn't keep us awake at night).
And despite this diligence, I'm still overwhelmed by the complexity of it all. We have managed to bump into more issues, bureaucracy, and unexpected fees than I ever imagined possible. And there are still loose ends that keep cropping up, months after our returns were submitted.
And we have smart, professional guides whom we're paying to help us. I don't know how the solo taxpayer can be expected to successfully submit an error-free return if they have anything other than the most simple of conditions.
In fact, there are so many judgment calls that must be made throughout the tax preparation process that one feels its practically impossible to be "exactly right." You get the sense that if the IRS wants more money from you, there are any number of ways they can find fault with whatever calculations you decide to use.
The feeling that keeps coming to my mind is this: There HAS to be a simpler way to do this. Where it takes much less time and cost to accurately pay one's taxes -- and ideally, where abuses and loopholes are much harder to perpetrate.
I'm not well-versed in the arguments against a flat tax, but I must say the concept appeals to me after the frustration I've been dealing with over the past year. And are there other models worth considering?
While part of the reason for writing this post is just to vent, I'm genuinely interested in hearing the thoughts of the PP.com community on this. Especially those of any CPAs/accountants/etc with informed perspective to share.