I came across a tax software for individuals who has been trading cryptocurrency for last year or two. I myself haven't made much sale last year thanks to the parabolic move in Bticoin as well as Altcoins so might as well riding on the uptrend. But I'm sure at some point I will think of taking some profit off the table and you should too.
Similar with real estate and stocks, as per some tax attorneys indicated, Cryptocurrency is treated as property and will be subject to capital gain tax from the viewpoint of IRS or Revenue Canada so we need to keep very good track of the buy and sell history. You may remember back last year Federal Court ordered Coinbase to hand over a good chunk of user record for another transaction over $20K or more so that they can see if the individual has filed income tax or not.
Bottom line is that digital currency world is not tax heaven and should not be used to avoid tax liability. The software/calculator on this website (https://bitcoin.tax/) will facilitate the bookkeeping work for you. You may transfer the record from any exchange to them and they will calculate it for you. You may have to pay a premium if the number of transaction of record is over 100, otherwise enjoy the free version :) . I haven't personally used the software yet since I don't have much to utilize now but if anyone has used or will use for this upcoming tax season, feel free to share your experience below for future reference.