How Complicated Are Your Taxes?

I'm single, I claim the standard deduction, I have no dependents, and the only other things I have are interest from bank accounts and some dividends from stocks. I feel like taxes aren't worth the stress. How about you all - how hard are your returns to get done?

Comments (30)

Feb 12, 2019

They are a fucking nightmare. Literally have a data room set up for it and have to pay a large regional to deal with everything. Took forever to find someone remotely competent too.

I'm Canadian and live in Canada most of the year but almost all my companies I have equity in are American which creates endless fusterclucks. I flow all the US income into a c corp there (here ATM?) to avoid witholding taxes but then paying myself gets kind of weird especially because it usually ends up being a weird combo of dividends and management fees going out to the holdco in each country.

One thing I will praise Canada for is that we have an exemption on cap gains tax for your first mill in cap gains which I think is a pretty cool way of encouraging entrepreneurs. Also our corporate tax rate is super low all things considered.

Feb 12, 2019

Taxes are easy when you go the route of civil disobedience, and simply not pay them.

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Feb 12, 2019

When you own businesses they get far more complex. 100% owner of an S Corp and partial owner of 4 LLCs. All the entities require their own tax returns which ultimately pass through income and losses to the personal return. Find a good CPA and it's stress fee. I don't even meet with him. I send my book keeper (S Corp) as she handles all the Quickbooks stuff anyway.

Feb 12, 2019

I made approximately 7,000 trades in Robinhood last year so things get hair for me for sure

Fuckin my way thru nyc one chick at a time

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Feb 12, 2019

Really? That's over 19 trades a day...

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Feb 12, 2019

Yeah baby that's how you get rich - haven't you seen the e-trade commercials?

Fuckin my way thru nyc one chick at a time

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Feb 12, 2019

The book keeping part takes the most work. I own a lot of rental properties and every receipt for every repair/purchase/service needs to be logged. No exaggeration I have around 800 receipts this year.

Once you have all the data properly broken down for each property the input is fairly straight forward.

Feb 12, 2019

Jeez how many units?

Feb 12, 2019

Enough that I buy random products for general maintenance/improvement by the pallet (light bulbs, smoke detectors, paint, flooring, etc), crazily enough I'm still picking up a new property every 8 or so weeks.

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Feb 12, 2019

All my investing is in shielded accounts (401k/IRA/Roth IRA) and I'm too much of a tightwad to give to much to charity, plus I rent. Because of this, I don't make enough to itemize b/c of NY state taxes. 30 minutes a year with a Dixon Ticonderoga #2 takes care of my issue.

Feb 13, 2019

Lets just say FATCA and FBAR are the bane of my existence... Even worse for friends who are Americans through a parent but have no real connection to the country. Would never give up my citizenship, but it is such a pain.

Feb 13, 2019

I am pretty straightforward - W2, a few equity investments, etc.. I used to do it myself in 30-45 minutes. About 5 years ago I got some equity grants and had a few grey area trades and didn't know what to do, so I got in contact with a guy I knew in high school that's a CPA that does taxes. Best $200 I've ever spent.

Not only does he save me $200 in an average year, but I also spend 15 minutes a year to hand him all my paperwork and then I sleep well at night. Plus eventually I'll likely buy a few properties through LLC, I'll have him handle those as well.

FWIW I am a CPA, but have never done taxes (disclosure: CPA license lapsed)

twitter: @CorpFin_Guy

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Feb 13, 2019

$200 for a CPA? Wow that's not much more than Turbotax...

Feb 13, 2019

that was exactly my logic, Turbotax is like $100+. Also, tax prep fees used to be tax deductible which was great.

He has DEFINITELY helped me save more than he's cost me.

twitter: @CorpFin_Guy

Feb 12, 2019

CPAs aren't too much, especially if you're not paying the name brand upcharge.

Feb 13, 2019

Super easy for me.

My wife goes to the accountant and gives him all of the paperwork. Is it easy for him to file in 25+ states?

Presumably.

Feb 14, 2019

I own an S-corp, personal income tax (income, some equity stuff, interest from different accounts). Huge pain in the ass...My accountant is really good so he's worth the money, but he's not cheap.

Feb 14, 2019

Family office + on/off-shore vehicles = complicated but worth it.

Feb 14, 2019
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