Yikes.
First off, you should not have tried three times to get
TN without bolstering your petition. You can get in big trouble for successively providing poor petition to different officers. I hope you can get better references THEN go back.
Second, while the officer was technically wrong to say you needed to get new TD's for your dependants... since you went to the trouble of bringing them along, then OF COURSE YOU SHOULD HAVE BEEN READY TO GET NEW TDs AS WELL. Your initial post seemed to imply that you were deciding whther or not to bring family, but if you were, then the convienient next time was RIGHT THEN.
As I said, if the family does not renew the TD at the same time as you get your TN, they will AT SOME POINT BEFORE THEIR TD EXPIRES, need to go to the border and get new TDs. No need to rush or be inconvenienced, but it does need to be done at some point.
Since you are having trouble with your renewal, you should be going by yourself, so you can focus on your TN application. Your description of last weekend could have got you booted out. woorying about TDs when you are at risk of being denied TN permanently shows a lack of understanding what your priorities are -- which is getting TN