My experience with trading reps, is that there are excellent ones and new ones that are not up on the rules.As I said, I did ALL of my transactions concerning the TFSA,s with RBC.

They may have different rules and it does vary from tech to tech( what they tell you that you can do and cant) It will not be flagged as a Deliberate Overcontribution if your broker has a 3 day settlement date.

http://blog.taxresource.ca/getting-ready-for-tax-loss-selling/

Maybe try googling the questions you have. Thats how I found a lot of my info.