Thanks for the help, this is online but will most likely be trying the desktop software for Mac to see if it will handle it.
Supposably TurboTax should be able to handle 10,000 individual transactions per brokerage account:
https://ttlc.intuit.com/community/entering-importing/help/how-do-i-enter-a-large-number-of-stock-tra...
It suggests that I can enter the summary info instead of each individual transaction so I'm going to look into this next as well.
Edit:
Going the summarized route by using a TurboTax supported affiliate "CryptoTrader" aka "CoinLedger":
http://cryptotrader.tax?fpr=o4466 using discount CRYPTOTAX10 to lessen the sting of having to pay another software :( but it at least sorts everything out. The downside is you'll still have to mail out one form that will show the IRS all the transactions.
If you go this route, they have some nice write-ups to guide you step by step:
https://cryptotrader.tax/blog/how-to-file-your-cryptocurrency-taxes-with-turbotax
