We’ve done all of your listed splurges in one form or another. Given the ages of your children, if you think you can stay in the parks late then I would plan on seeing WoC and F! at their second showings and not spend money on dining packages for a spot on the ground. But if you aren’t sure you can do second showings, I would probably do the RDZ dining package for F! since it’s the most reasonably priced and has food they might actually like. We did a F! dining package once (Hungry Bear at the time) and decided we’d really rather not sit on the ground at our ages. I’d be willing to try out the RBT premium viewing package if I were able snag a reservation.
For BB, I think it depends on your kids. Mine have eaten at BB several times (as toddlers and teens and ages in between), and I don’t think it really has ever been that special for them. My best meal at BB was my most recent, when DH and I went alone for the first time in 25 years. We did politely request a table on the water, arriving early for our reservation and letting the host know we were willing to wait however long it would take. This wasn’t our first water front dining, but it was our first without kids. My kids weren’t the type to only eat chicken tenders, but they also didn’t care for a lot of unique spices and sauces. (That said, they loved Steakhouse 55 when it was still around — both the food and the ambiance.)
WoC dessert party was a one and done for us, and that was without our kids. I loved having a place to sit, but it was a lot of hassle to wait in line to check in to choose the table, and then wait in line again to be seated. I felt like we lost a lot of time. The kids at the table next to us did seem to be having a good time, however. My kids would have wanted to be up and moving, and wouldn’t have liked most of the desserts. They are perfectly happy with the VQ.
My kids at the ages your kids are now are fine with standing, and my antsy youngest would rather stand that sit. Any money I would have put into a fancy meal or dining package they would have rather had for souvenirs. My youngest was 19 when SW:GE opened, and saved money to go to DL with friends and to do the lightsaber workshop — that was their kind of upgrade experience (friends didn’t do the workshop). If they had been younger when it opened, that is the kind of upgrade they would have wanted me to splurge on. My oldest is my true Disney nerd and is now a proud Disney adult. They love buying shirts and pins and have put together several themed lanyards over the years. I think their idea of a splurge would be a guided tour where they get to do something not everyone else has done. The railroad tour doesn’t look to be going right now, but that would have been right up their alley (we have ridden in the Lily Belle more than once, but that’s no longer free). Probably getting to see Walt’s apartment would have been fun for them.
For my kids, the most memorable things have been things that just happened, mostly by being aware and polite. Being in ToonTown late at night when it’s nearly empty and spending 10 minutes playing with Pluto. Any of their unscripted interactions with characters (versus waiting in line). Checking out the Lily Belle when it was stationary in NOS and being invited in for a private tour in honor of an 18th birthday. Being on Big Thunder as the fireworks light the sky (that takes a little planning). Getting to meet their favorite horse while he was waiting for passengers to load. Being singled out by a member of the
DIsneyland Band and asked their favorite attraction, and in general being recognized by the band members because we see them as often as we can. Getting to play a rag on the piano at Coke Corner for an audience because they were interested in the performance and took a moment to thank and talk to the piano player. Having one of the small bands play Happy Birthday for them when they saw their button. Getting to know the players of the jazz band (again because we saw them every time we could). There are more, of course, but some of the opportunities don’t happen anymore. Me paying for a dining package can’t compare with being chosen — together — to become Jedi knights.