Watching Star Trek from start to finish will take a huge amount of time and if I ever finish I will have spent more time watching Trek than any other series. I'm fine with that and plan to take my time. TOS is old and when you're watching a show like Game of Thrones at the same time it really shows. Yet even with all the cheesiness I'm enjoying most of it. Even if lines like "NO BLAH BLAH BLAH!" are hilariously bad.
Skipping to TNG, or just watching the best episodes could work; but I want to watch the show and if I'm going to do that I want it to be in the best possible quality. That means buying the blu-ray set. If I'm buying it I'd be crazy to skip most of the content considering the price. Also nobody else knows what I like. If I listened to recommendations and only watched the episodes other people think are the best I might miss my favorite.
My TOS set should arrive at some point today and I'm looking forward to watching the show in 1080p with 7.1 surround sound!
I have more than enough Trek to keep me busy for a very long time and I'm crazy for asking this: Are any of the Original Series books worth reading and what do you recommend? I'm only interested in reading one or two of the best because I'm guessing the quality is even more varied than the show itself.