@JordanHanks I'm not sure who you talked to or who you emailed. But, when I had an issue with equipment last year and wanted to cancel my year subscription to Channels I just emailed support they helped me out with no hassle at all. Once I got my equipment issues resolved I signed up for the year again and things have been fairly smooth.
Yeah no one has said Channels won't be nice and prorate. I was just saying it's wrong to assume they should and personally I never would expect it. I'm the one that decided to pick the year sub for the reduced price. It's for that reason I'm currently on monthly. I just started using Channels DVR, and I wasn't sure it would work well, so I'm on month to month for awhile until I decide if to cancel or go to yearly. So far I'm enjoying it and leaning yearly 
In another situation, I got screwed out of $160 because a yearly sub I didn't want renewed. I told them 2 days after it cleared. They wouldn't give any of it back. That's more shitty, but I still blamed myself for not staying on top of my subscriptions more than them not giving it back.
So right. Technically, you are cancelling the 1 year re-sub date. So you continue to have your sub until the date of the one year renewal hah.
Personally, I think anyone starting a new subscription service should join month to month to find out if it fits their needs before going all in. I've tried many streaming services I thought would be a great fit, only to find out that wasn't the case. I also think it's wise to make a point of asking in communities such as this or emailing the streamer directly and asking them their cancelation and refund policy before going all in. There are a lot who will cancel your account but tell you that you have the service until the term runs out.