We are going to get a release of Outlaw Star, it's just for some unknown reason, Sunrise
still hasn't sent the materials to FUNimation and they've been waiting for them since
late 2013... This is one of the longest materials delays in R1 history. Sentai Filmworks has it even worse, they've received materials for
nothing, at least FUNi got Escaflowne, Code Geass, and Cowboy Bebop out the door.
As for licensors giving companies inferior masters, I doubt that's the case today, but it was a thing back in the DVD singles era. Kadokawa intentionally sent companies composite masters for Scrapped Princess, Full Metal Panic? Fumoffu, Maburaho, The Melody of Oblivion, Girls Bravo (which for some odd reason still looks like crap through FUNi and I don't know who to blame, FUNi or Kadokawa), and some more I may be forgetting or don't know about. Scrapped Princess in particular
looks atrocious. Once Kadokawa Pictures USA happened (they're long gone now), we got clean video on Kadokawa stuff.
As for the high-pricing, they deal with it because they have an inelastic demand and are buying right away + Japanese releases are much nicer in terms of packaging, not just video quality (in most cases). They're not going to wait for a barebones release that comes out 6 months to a year or two after the Japanese release finishes that has locked subtitles and/or geo-locking. Also many are aware that if they don't buy, the industry could collapse or have issues. Video publishers tend to be at the top or towards the top of the production committees they're on, and are investing quite a bit, though the discs aren't the only thing that matter of course.