TD-
capital gains and dividends
I only have 2 stocks, Company A & Company B.
I decide to sell, make 10k on one, lose 10k on the other. My losses offset my gains, so, no capital gains tax there....still have to declare and document it on my taxes.

But, Company A paid me 3k in dividends, which I will owe tax on

I think this is a great post Duck, being a pilot our lives are not as easily fit into the boxes that the IRS has. In any case

Caveat emptor

The opposite is somewhat true also. The CA Franchise Tax Board may try to collect from you if you are domiciled in CA and live elsewhere. In the end, you won't have to pay, but they sure will try their best to get their hands on your money.

California is VERY aggressive. I've heard something about calculating the actual time you spend in CA airspace but have never bothered to confirm it. I've heard if you spend over 50% of your flying time over CA you are liable for CA taxes but find it hard to fathom. Perhaps someone else wants to look it up.

Itemizing Dry Cleaning?
 

First, yes, I know this thread is ancient, but I've looked for way too long on the net and here on the forum, and still haven't found an answer.

Here's my question: If during the tax year I have actually been to/paid for 36 visits to the cleaners for dry cleaning uniform items but only have receipts for 20 of those visits, can I still deduct all 36 visits? Not sure about this whole "$75 or under" rule from the IRS. One source said that rule only applied to entertainment and meals and another source said it applied even for NON-entertainment and meal expenses if you have "some" of the receipts but you can show a clear pattern of spending (like paying a dry cleaning bill the day before a trip starts) and have some kind of supporting documents (like your company's list of all your trips in the last year), then that would suffice.

What say you? Any CPAs masquerading as pilots out there?

Thx in advance!

(PS - Yes, I know the easy fix is to make sure I save all such receipts. Didn't know dry cleaning was capable of being itemized until half way through last year.) :rolleyes:

Doesn't matter anymore because the tax reform got rid of the employee business expense deduction.

Crypto
 

How should I treat my losses in the crypto account this year?

https://btcmanager.com/gigawatt-bankruptcy-washington/

As a learning experience, hopefully.

I am going to start a mutual fund. My research will be combing pilot forums, surveys in crew rooms and input from individual pilots.

And then I am going to short the crap out of everything that pilots are investing in.

PISF. The Pilot Investment Short Fund. Coming soon to a brokerage near you.