I have done a lot of soldering over the years, and was trained to do it by old Ma Bell of the Chesepeake area, and got years of practice doing it afterwards. I also did buy the silver coated connectors, but I still think it's worthwhile running a file over them, which I did not do this time. However, the way the solder flowed into the holes was a pretty good indication that it "took" this time.
Lil'Yeshua, the Weller 200/260 seems to be hot enough that you do not have to take so long doing it that it heats up the whole connector. That's why I don't like the liteweight gun I was using, it melted solder, but it had to heat the whole connector to do it and still did not "draw" the solder in. This new gun does it in just a few seconds. And I thought of it, but forgot at the end, to use a square of folded up wet paper towel to cool the connector down after soldering. That should help save the teflon insulator.
By the way, I am glad I checked my local Ace Hardware. I found the Weller gun, a kit box with some solder and two extra tips of different sizes, including the big hefty chisel tip that was mounted in it. And are you ready for this, it was $20 cheaper in the store than anywhere I found it in 4 days of searching online.
Thanks guys for all the comments, I learned something again.