Pleasure Island has, to me, become one of Disney's more bizarre failures, probably because they didn't stick to their original mission statement of providing a fun-but-secure onsite venue for just grownups, plus an attractive locale for locals to come and get their drink on. When it was opened in 1989, Disney as a movie studio was starting to invest more heavily in creating some adult-themed entertainment, and PI was a reflection of that. Now, nearly 20 years later, the social landscape has changed, the new generations of clubbers are perhaps not represented by what PI is, and Disney has muted its presence in producing entertainment that's not family-friendly. So aside from us diehard AC fans who'll also venture off into CW once in a while, there's not too many people for whom PI will represent a fun night out. Parents who wouldn't leave their children behind certainly make me uncomfortable, when I see little ones in clubs like 8-Trax or the now defunct R&RBC, just as I'm uncomfortable seeing them in any resort bar/lounge area. If you're going to WDW and your children aren't old enough to venture off alone, then don't go to bars or lounges or PI with them.
I never went to WDW as a child, but in the family trips to SIx Flags Great Adventure, simpler less child-abductier times, it was common for an older brother or sister to take command of me and/or my slightly-older sister (we being the babies of the 5), and it was "OK, we meet back at the fountain at 6 o'clock, don't be late and don't get in trouble."
But as far as PI goes, this is like a chicken-or-egg type thing. Did childless adults stop going to PI because kids were there making it weird to party like grownups do? Or did WDW start allowing parents with kids in tow to go into some of the PI clubs because adults stopped going?
If WDW were to provide adults-only lounges in most or all of the resorts, I'd suspect that might go over better with the mentality of today's modern family. Parents might feel more comfortable having a drink or two knowing the kids are nearby in the room sleeping, or, if they can be trusted, in the pool or arcade areas. It might also inspire some people to resort-hop and see what each lounge has to offer. Someone who's usually stayed in values or mods might decide to "bump up" to a deluxe on the next trip if they had a nice enough evening in one of their lounges. If this were the plan, I'd humbly suggest (at the risk of taking even more money out of the local economy), the time might be right for WDW to develop it's own intra-resort taxi service. This way, adults who want to go from resort to resort can do so without waiting for a bus to take them to a hub and then another bus to take them home. If, instead of a central location, cabs are dispersed throughout the resort area, so there are always cabs coming and going and nearby if not actually where you are (with a dispatch moving cabs around if there are too many at any one resort), it could really become a cash cow for WDW, plus provide the guests more opportunities to do more at WDW without paying for a rental car (and also, not risk DWI).
I'll miss PI much the same way I miss many things I enjoyed from my past. It's not what it used to be, but then again, neither am I.