I play the every 6 month game too, have been for years...but sometimes I have to let my subscription expire before I can get the $25-$30 deal, but most of the time just threatening to cancel due to full price does it.
However, I just learned a new trick today. I had a little bit of prepaid time on my last 6 months for $25 left over on my 2014. When I went online to cancel that account, I found an option to transfer that balance to the end of your new trial period for the 2017. In the process of doing that, it offered me the option to extend all access for 6months for $49.99 OR the select package for 6 months for $29.99. I dont need all access because I dont stream or care about the 10 channels that come with all access (MLB, NBA, PGA, etc...). Select has Stern and all NFL and all the music I want. The best part was I didn't have to call and sit on hold and play the game with anyone.
FYI, the way the transaction ACTUALLY worked was different than what it said online. It was super simple, like 3 clicks, under Help and Support when you go into your account. It says transfer service to a new trial subscription. What is actually did, was delete my old radio from my account, refund me like $11 on my credit card and set up the 6 months for $29.99 to start at the end of July when my trial ends (and they wont bill me until then). Very fast and VERY easy. Hope this helps.