1) $395 is a package so you pay $395/yr even if you have only one trade in the year. They do prorate the fee and trades if you enroll during the year
2) ONLY charge you ONCE for multiple orders on the same side for the same stock in the same day. So if you buy the same stock 10 times during the day at different prices, CIBC only charges you once, say $6.95 if above 50 trades. Buy and Sell the same stock are considered as 2 trades.