Well, Carol went almost all the way when it came to award nominations. Yeah, Gray's last two films were melodramas that were heavy on subtlety and restraint (I haven't seen Carol, but it sounds similar in that way), so they probably wouldn't have found a big audience even with strong distributors/promotion behind them. But his sensibility is also far from alienating, and if he made something widely acclaimed and at least given a chance at the box office, I don't see why he wouldn't get award recognition. Then again, it's really hard to tell with Lost City of Z because it's a very different genre and budget than he's ever had before.