I'll second Mere Anarchy. It's not only a great read that spans the entire time Kirk & Co. are on the Enterprise, but it has some stories that fit in the gaps of the timeline where we don't know what happened. Shadows of The Indignant by Dave Galanter happens in the "Lost Years" era between the original 5YM and TMP; The Darkness Drops Again by Christopher L. Bennett happens between TMP and TWOK, and the afore mentioned The Blood-Dimmed Tide by Howard Weinstein, fits in between TFF and TUC. It was an all around great series. Hopefully more ebook series like this get printed in the future
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hm.. I was going to put this one off because of the sheer length of it, but I may have to succumb...