What I find is that a solid .Org domain is a development catalyst.
All the usual difficulties attach to developing a prime .Org, but so long as the focus is on user value/experience - and not simply attempting to exploit the address - the .Org address may smooth certain hard/sharp edges of the development climb.
YMMV, but from my POV development needs to track the spirit of .Org to sustain any boost the gTLD may provide.
Blackjack.org? Poker.org? Sure, IF they really dig deep into the education and the reality of the game and industry, whilst going light on the commerce.
If memory serves me, CraigsList.org does very little commerce, yet the staff and the bills are paid . . and Craig also has a bit of personal economic security, too. ;P