The 2020 Guide To Cryptocurrency Taxes by Lucas Wyland ...

[uncensored-r/BitcoinMarkets] Some questions about taxes, bookkeeping, and GDAX / coinbase records

The following post by throwaway929892988 is being replicated because some comments within the post(but not the post itself) have been silently removed.
The original post can be found(in censored form) at this link:
np.reddit.com/ BitcoinMarkets/comments/7ly39l
The original post's content was as follows:
** I know this is long - if you are able to answer any, or a few, of the questions contained in this post, I would be extremely thankful. Really any comments would be appreciated so I know I'm not alone**
I've read all the threads on this and other subs regarding taxes, and recently bought a 1 yr. subscription to cointracking.info. Unfortunately, I purchased ETH, LTC, and BTC via coinbase for the first few months of my trading, until I found out that GDAX is so much cheaper and easier to use.
So I have records in CSV format from both exchanges, similarly, cointracking.info couldn't seem to reconcile (whether using CSV imports or API data) my various transfers from coinbase to GDAX for my day trade attempts and from GDAX to coinbase after purchasing, and before transfer to a hard wallet. So it interpreted these transfers as "sales."
I've also sent a handful of ETH to binance to put into various alts (which are all currently down). I recently day traded a bit with BTC while it was falling predictably down and increased my holdings by .05 or so. I wasn't thinking, and now realize that this effectively "realized" my gains on part of my BTC that I had been buying since early August. I repeated this process quite a few times, buying and selling the same sum of BTC.
  • However, what I don't understand is how one is supposed to "pair" or decide which portion of BTC they realize when they sell. Because I bought BTC all the way up from around 3 K and if I technically realized the gains from some BTC I bought at 9 or 9.5 K during my trading / realizing, then the tax I owe would be a lot less than the sale of BTC bought below 5, etc. Is this discretionary - I know there's means to I.D. specific coins, but when I sold it was certainly a varied mixture of *hundreds of different small purchases.
  • I'm also having problem even using the GDAX CSV of sale records, because of some recent day trading, my technical cost includes duplicated "re-buys" of day traded coins, so it thinks I spent like 7 times what I really did, when in reality I was buying / selling the same bundle of coin / coin fractions.
  • With my limited understanding of taxes (recent college grad with no job yet) I'm hoping that for some of the day trading, it will at least only be the first (of a handful of buys and sells with the same coins) that are realized to cause any substantial tax costs, as once I sell and re-buy once, my basis is now much higher, and given that I was selling and buying in the same general price range of BTC (and other coins) the spread / difference would be comparably minimal, so it's not like it takes the same 25% or whatever percent each time I make a trade, right?
  • Lastly, does anyone know how capital gains from conventional stock portfolios affect your tax bracket? I may have read that some people qualify for 0% tax on long term gains if they have no job, and meet a few other variables. I currently have no earned income, but do have a relatively large stock portfolio which I oversee with a family member, the markets done well this year, but to my knowledge none of this large and varied volume of stocks are ever sold / realized, they are just being "hodled" for lack of a better word, as many do in traditional investing.
  • Having acted out of greed / opportunity and naivete (thinking I was helping myself + making money by buying before a dip and buying back, I will never day trade again. I only hope that these taxable events do not eat up a huge fraction of my gains, which I have worked hard to accumulate while working diligently to learn the ropes of crypto buying and research. I'm not asking for sympathy, as I have it better than many, but I do seek information and want to have some general questions answered before I go back with a giant excel file to bring to my family friend, so I can ensure the information is accurate, etc.
I luckily have a family friend who helps do my parents taxes in exchange for dinners and out of generosity. I approached him with questions about how to "track" my gains off of ETH into binance alt coins, as the price of ETH shifts constantly, and we ended up talking taxes. He asked me to chart every transaction - volume, price, date, fee, coin, etc. in excel - I had been doing this fairly well for months, and think that combining the coinbase and GDAX CSV files for each 3 coins might work, but it's so much data I'm very stressed - and equally pissed if my day trading stupidity (which earned me 500 dollars) ends up costing me 3 K in taxes.
I know this was a lot of varied questions, and I'm happy to re-format in more palatable bullet points, but if anyone is willing to answer any of the above confusions I would be very thankful and would find a way to give thanks
Thanks for your time - a concerned / born again hodler
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