I'm holding off until there are full series sets of everything for less than $200 a piece. I don't care if I have to wait until 2100.
You'll probably have to wait a lot longer than that.
Yeah, less than $200 each is a price that not even the DVD sets have reached, and they've been out for nearly a decade! As far as everything being available in HD, well... looking at just the series that require remastering, to date CBS have already put out 101 TNG episodes and they take about a week per episode to complete at this point. So there are 77 episodes left of TNG to release (they're actually done with S5, so there's really only 52 episodes left) and 176 DS9's and 172 VOY's. Now assuming they don't farm out any work like they did with TNG, it would take CBS Digital another 400 weeks or sometime around spring 2021 to finish!
The TNG-R project started in summer 2011 and will finish around summer 2014, so it will have taken them 3 years from start to finish with two other VFX companies helping out on two seasons. Basically CBS-D did about 75% of the work. So, at minimum, there's got to be at least another 7 years left to go. Not quite 2100, but