When you set a milestone you're essentially giving the Transmission team orders on what to work on, and on what timeline they need to do it. Don't do that unless you're going to cut us paychecks. ;)
Now, about the https issue: this was also reported in this forum thread and I'd be happy to look into the matter. However, it's working for me every time I test it. I need more information before I can get any further with this ticket.
Options:
(1) Send me a .torrent file of yours that doesn't work. Don't attach it here in trac; send it to me privately to charles@….
(2) From a terminal, set your environment variable TR_CURL_VERBOSE to 1 and then start Transmission in that terminal. libcurl will dump its debugging messages to the console, and you could mail the that output.
