Unless you have 30 different funds, it would be better to ask your investment advisor for a gain/loss report, which will provide more accurate costs, and probably summarize the activities. The T5008 is an advisory to CRA that transactions have taken place rather than a required slip for your T1. Some T5008's are quite good, but often they do not show an accurate cost, or do not show a cost at all.
I am in the same situation. I am shocked that the software has this limitation. As a long time Turbo Tax user, this will be my last purchase
Unless you have 30 different funds, it would be better to ask your investment advisor for a gain/loss report, which will provide more accurate costs, and probably summarize the activities. The T5008 is an advisory to CRA that transactions have taken place rather than a required slip for your T1. Some T5008's are quite good, but often they do not show an accurate cost, or do not show a cost at all.
It definitely works when you use a Gains and Losses report and not use the T5008. It is the same info and you enter it on Schedule 3. A few lines can be put on page 1 and then you put all the rest on Supplemental Page to Schedule 3. Works just fine and all the numbers transfer where they are supposed to. Just be sure you do not enter a T5008 plus the Schedule 3 with same info. Worked for me.
Great answer and a good warning about double reporting.