SAFD:
If I go back to my favorite years of visiting WDW (about 8 years ago)....
Justified:
-Annual Passes. We live out of state but would get APs and come multiple times, for shorter trips, in a year. Then take a year off and do it again. My kids never loved being away from home for more than a week at a time and with the ticket prices being more expensive per day for shorter trips, it was worth it.
-Rental car: Back in the day when you could park at the resort for free, it was worth it to be able to drive right up to any park but MK and come and go as we please without waiting for a bus. Shoot over to DS if we wanted, it was a lot of freedom.
-Deluxe resort: Staying right there in the magic was worth every penny, back when it was a few hundreds of dollars cheaper per night to do so. One of my favorite memories to this day, is being in Stormalong Bay late at night with my older DS, sitting in the pool, seeing the tops of the fireworks from Epcot, playing ping pong too, etc. It felt like the hotel stay was an extension of your park day. It felt like the fun went way into the night, and outside, you could be in the middle of it the whole time.
-WDW itself: When our kids were younger, it was expensive but still a great value. You were absolutely guaranteed your kids would have a good time, no matter what, which is priceless. We had taken a few big vacations outside of Disney when they were young, like a cruise around the Mediterranean seeing the sights. The kids had limited appreciation for historical landmarks, and by the 8th day one of them said they were tired of looking at "dirty cities". We have gotten some flack from our "sophisticated" friends and colleagues for taking so many Disney vacations but when you have kids (up until recently at least) it was money well-spent because it was zero-risk for a family vacation.
These days, all of these things are feeling unjustified to us. The value of the deluxe stay has whittled down the most for me. Over the years, the prices have crept up and the amenities have crept down. Stormalong Bay closes earlier and earlier, to the point where, the last time we stayed there, between the early closings and the thunderstorm closings, we didn't use the pool once. Housekeeping kept getting scaled back (even pre covid), and you start to question why you are paying so much to stay when you aren't even getting housekeeping every day. When we stayed at a monorail resort a few years ago, all the bars closed shortly after the parks closed and there was nothing to do. I guess they wanted you to go to DS or the Boardwalk? Then why stay on the monorail?
As for APs and rental cars, the increase in pricing for both of these plus resort fees to park make it less worth it.
We are using up our APs we are holding currently, seeing how the value is looking for our MW and Princess trips, and then making decisions based on how things went there.