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?

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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.

 

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.

 

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.

 

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.

 

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.

The only difference between Asset Management and Investment Research is assets. I generally see somebody I know on TV on Bloomberg/CNBC etc. once or twice a week. This sounds cool, until I remind myself that I see somebody I know on ESPN five days a week.
 

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
 

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
 

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