You need to break it down further than that.
Watch the first 5 seasons of TNG, then watch season 6 along with the first season of DS9 and TNG s7 along with DS9 s2.
DS9 s3 and Season 1 of Voyager next, then watch Generations before starting DS9 s4 and Voyager s2.
Watch the first 9 episodes of s5 before watching First Contact then finish the season and catch Voyager s3.
Ds9 s6 & Voyager s4.
You can watch Insurrection at any point before the end of DS9 (somewhere in the middle is good).
Finish off Voyager before seeing Nemesis.
I'd leave enterprise and the new movie until after all that, 'cause there are a lot of winks and nods
And yes, I'm one of those weirdoes who liked Enterprise

Season 4 was some of the best Trek ever, and I can only imagine how good season 5, the Romulan War and the birth of the Federation would have been.