According to Bryan Courchesne from DAIM and Saim Akif from Akif CPA, crypto tax preparation requires year-round tracking due to unique features like no wash-sale rules for efficient tax-loss harvesting and direct asset swaps such as BTC to ETH. Challenges include incomplete cost basis tracking on centralized exchanges like Coinbase and manual logging on decentralized platforms like Uniswap, which can lead to IRS audits if not managed with crypto tax software or specialists.