Taxes/IRS Make Me Want to Blow my Brains Out!

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Jul 26, 2021
2,419
9,818
Metro-Detroit
Not only is it a P I T A to do your taxes, you have to pay to do them.
Best tax advice I ever received was "taxes be damned" followed by an offer to pay the taxes in exchange for the money received. Taxes be damned, indeed.

As for the tax preparation, either buckle down or pay a CPA to handle the grunt work. The cost benefit analysis may reveal a $300 tax preparation bill is worth saving the time and headaches preparing the taxes yourself.
 

PipeIT

Lifer
Nov 14, 2020
5,238
30,880
Hawaii
You obviously never had to deal with a 1099-B and ISO stock options. (I am grateful and lucky that I do as the extra money at this point in my life is nice). But if you want to persist in assuming I am an abnormal worker that is your choice :) . If you were my neighbor you would think otherwise seeing me leave at 6am and returning after 5pm everyday and working weekends to boot. Of course we may have different definitions of "normal" and I certainly respect that as I respect you. Cheers (with a manhattan)!!

I haven’t had to deal with these, but there are no options for these on Turbotax? 🤔
 
Jan 30, 2020
2,329
7,690
New Jersey
I’m still confused why stock options are taking so much a dime and generate 230 pages of tax forms. I have gotten restricted stock units for about 10 years now……..Morgan Stanley gives me a 1099-B, I enter the info into TurboTax, and it’s done.
 
I’m still confused why stock options are taking so much a dime and generate 230 pages of tax forms. I have gotten restricted stock units for about 10 years now……..Morgan Stanley gives me a 1099-B, I enter the info into TurboTax, and it’s done.
I know - this is not an RSU - those are easy. This is an ISO situation with AMT (with adjustments, bargain elements, etc). Plus the way fidelity and my company recorded it is contributing - it's not all turbotax but turbotax is clear as mud. mathematically I get it all but how to enter it is agonizing
 

jguss

Lifer
Jul 7, 2013
2,687
7,396
As the old vaudeville sketch refrain ran, pay the man the two dollars. You’re on a self-inflicted crusade that is unlikely to end well.

I haven’t done my own taxes for over thirty years. I don’t care how cheap you are you’re better off getting a good accountant and dumping it on him. He not only does all the work, if there are questions about your return he handles them on your behalf. Don’t you place a value on your time, mental energy, or peace of mind?
 

Briar Tuck

Lifer
Nov 29, 2022
1,109
5,744
Oregon coast
I’m sorry, that’s just not true. We have investment income, my wife’s full-time job, her very profitable Etsy business, and my full-time freelance writing. I did it all with the standard version of TurboTax.
Well, I always start with the standard version and Turbo Tax insists that I need to upgrade due to my tax situation, which is really only divided and interest income, and sometimes a stock sale, nothing else. Maybe I could indeed accomplish it with the standard version, but Turbo Tax says otherwise, every year.
 
I don’t care how cheap you are you’re better off getting a good accountant and dumping it on him. He not only does all the work, if there are questions about your return he handles them on your behalf. Don’t you place a value on your time, mental energy, or peace of mind?
Haha - yeah - I'm stubborn and I live to conquer problems - in fact that is how I make a living - solving problems. It was a "rant" - I can deal with it. Just having some fun with my fellow pipers I guess. I had a bad experience with an accountant once and never again. I am not that desperate yet. When I do figure this out...and I will, I will be damn proud and I will have learned something for next year. Oh God! What if the tax code changes and everything I learn is kaput!!
 
Regarding audit - If your tax return does not contain red flags it is unlikely to be audited.

The common type of red flags

1. Not reporting 1099
2. Too much itemized deduction for dubious expenses. I have also seen unscrupulous accountants putting in dishonest itemized deductions, betting on the probability that it will not get audited

If you are honest (and your accountant is honest) you have nothing to fear.

I have done my taxes with a human twice.

1. The HR block guy was knowledgeable and did it properly but I had to wait one hour on the first day and then was sent back stating that they are overloaded. The second time I had to wait another 60-90 minutes before I got to see him

2. When I was younger I once picked up an average Joe off the Main Street. The return was so bad, I had to discard it and manually file it myself again
 

sablebrush52

The Bard Of Barlings
Jun 15, 2013
21,015
50,366
Southern Oregon
jrs457.wixsite.com
I stopped doing my taxes years ago and use an accountant. Keeps my blood pressure from going through the roof, though I hate the cost. I list all my expenses in a neatly tabulated format, keep scrupulous records, but just don't have the time, or the patience, to deal with the investments and other complications.

I did get audited back in 1985 on my 1983 return. That was a real learning situation. Especially for the auditor, who must have been longing for death by the time I got done with her.
 

kcghost

Lifer
May 6, 2011
15,138
25,715
77
Olathe, Kansas
Being retired this is pretty simple for me. I only do my own state. So, mine is simple as can be. Still takes a couple of hours. As silly as it seems you should at least be comforted that if it was twenty years ago your tax work would have been 2 to 3 times as hard.
And you're being foolish to not have a pro prepare it for you.
 

captpat

Lifer
Dec 16, 2014
2,388
12,411
North Carolina
Three key folks for me: financial planner, accountant and a lawyer. I don’t need much from any of them but they make life easier, especially in timing IRA distributions
 
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mso489

Lifer
Feb 21, 2013
41,211
60,638
First a debilitating charge for taxes due for 2021, and then an additional withering charge from 2020. My tax preparer has sorted out the explanations and helped some with the totals, but it is not a reassuring picture. Translation, if you financial consultant does a good job for you, it may not mean happiness at tax time.