YTTV rep the other day and she said if the content in your library says "released XX days ago" or "released XX months ago" that it is Video on Demand (which I take to mean that there will be commercials that you can't skip). If the content in your library that you want to watch says "recorded XX days/months ago" then it means it's not Video on Demand (which I take to mean that you can skip commercials).

But, you're right. Some of those things you mentioned can be annoying. I was a little peeved about the NFL preseason game being blacked out because my local affiliate or whatever didn't obtain streaming rights. I know the regular season should be different, but I won't hesitate to go back to cable if I'm not able to watch sports how I want.