I shoot the Winn Free Flight Glove C10 and have shot it for years, I have shot it off the string and find it works very well with a string loop.... it just takes sometime to learn how to load and lock the release head on the loop its a bit of a pain in the beginning to master.The curved and polished latch on the release head that holds the string seems to allow the string a smoothly slide off the latch and out of the release head.
I tried the Winn SS Caliper and sent it back.... I found it to feel not as smooth a release to me as the C10, but this may also be attributed to the fact that I am used to the C10 having been shooting it for many years.
As for the trigger I found that it can be easily shot as a back tension if you get the trigger in the 2nd joint( joint closest to the knuckle),of the index finger and this has worked for me to solve the trigger punching.