Ive never tried to import, data entry is the quickest easiest part of our job, in the time it took you to hassle with the import that didnt work, or to verify that what you did import landed in the right spot, you could have keyed in the numbers.

I do enter a lot of stock transactions, but not when there are over 100 pages of them

Most of us summarize by brokerage, short or long non covered, covered transactions can go in the summary boxes at the top of the 1099B...its rare I have more than 2 or 3 entries for any one brokerage.