My specialty is working all the angles so here's where I am with things.
I called WDW-DINE again tonight. The largest group I can personally book for TE is 30. She also told me that we can't technically book until Sat Oct 8 (that's officially 90 days) so we have a couple more days to flesh this out.
One thing I've learned about Disney...you get a different answer every time you call. So I called TE directly and spoke to my new friend Paul. He says the largest group they can seat is 20, but I tried a bit of whining. He said they may be able to seat 50 if we're trying for the first ressie at opening time. He's going to do some checking and call me back tomorrow if they can handle our group. If they can, we'd still need 4 or 5 people to book their groups individually. But I think that might work well if Paul can help us out.
I kinda like Bree's idea...let's keep this going until we hit the wall, then we can look to other options if needed. I'm also intrigued by Lynne's idea...does anyone by chance have a DVC ressie in a grand villa? I bet we could all fit in there and bring our own food. We'll have our van and can pick up takeout.
And there's still the food court option...they certainly won't turn us away since they don't take ressies. POR or POFQ would be cool. Pepper Market doesn't require ADRs to my knowledge, but I always thought their ticket system was weird. Don't know about CBR...I haven't stayed there in years.
I'll let y'all know when I hear from Paul. Until then, no need to call for ressies til Saturday!