How Complicated Are Your Taxes?

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.

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

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.

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

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.

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.

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.

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)

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.

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.

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