Generally all the 'dark cherry'/'tobacco'/'plum' etc. flavors are kind of meaningless to me. I rarely detect anything I think I can pick out, I just tend to decide if I like the taste or not. Usually the nicer the wine smells, the better it tastes, sometimes its 'fruit forward' (sweet), sometimes it's 'tannic' (bitter acid) and sometimes it just burns (alcohol content).
What I believe is bullshit is the people trying to describe flavors in a wine and extrapolate quality from that. If you like a wine, buy it, if you don't, don't. I enjoy some cheaper wines (Chariot Red at Trader Joe's is a fine value for about $5 imho), but my own tasting notes do indicate some $60 bottles of Pinot Noir taste way better to me than average. However, there are also some $60 and $150 bottles I don't think are very good.
As for wines tasting alike, if you can't taste a difference between grape varieties, I guess stick to Charles Shaw and enjoy. I wouldn't be surprised that the experts have a hard time with multiple tastings, as the wine taste changes with exposure to oxygen, on top of the tiring palate.