We've "planned" trips to WDW only for me to decide against it because I start to second guess everything. In researching it seems to me that WDW has more restaurants, shops, and shows, (and actual parks of course), but as far as ride attractions go, DLR has more. I don't love Disney food enough that the many restaurants lure me, nor do the shops...as much as I love Disney, I am not one of those people that has a Disney themed kitchen or drips Disney products (I think I own two tee shirts and a hat) so except for a browse through shops and purchase here and there the shopping doesn't lure me either. The sheer size of WDW as a whole frankly turns me off, size is not always better.
I don't know if I'll ever be able to bite the bullet and go for it ... I am a planner and a pretty patient person, but the cost is so much greater for us to get to Florida, then there's the weather (humidity, monsoon rains, etc.), massive crowds, and I see people talk about the Disney bubble, but for me I don't see how everything being such an undertaking, getting from hotel to a park, transportation delays, long waits with throngs of people dripping wet from humidity or rain for for buses, Minnie Vans, or ride share or rental cars would make me feel like I'm in a bubble at all, much less a Disney one. We don't stay onsite when we go to DL, and it doesn't bother me one bit, now if money was absolutely no object of course I'd stay onsite, and I can see understand how for some people they will only stay onsite, but I personally am just fine outside any conceived bubble. Then the whole Fast Pass system there sounds awful. I'd be so disappointed to spend THOUSANDS of dollars on a WDW vacation not to be able to ride every ride I wanted to during our trip and having to use Fast Pass for character meet and greets too, UGH! And no New Orleans Square, well I just can't even fathom...
I think I am one of those that probably should just stick to DL, Walt's original park - when I read people comparing the two I sense that I would be horribly disappointed by so many things at WDW that the trip would frankly be one that we'd never wish to repeat and I'd be mad we didn't go to Europe for the same price (fake European countries at Epcot don't excite me - although fake New Orleans at DL does...haha). In addition my kids have grown up going to DLR so we have all those magical memories ingrained in us and I think for most people the park they grew up going to is where the magic lies, although even many frequent WDW park goers often give the upperhand to DL when comparing MAGIC only simply because of Walt's hand in things and the attractions that only exist in DL.
Maybe I'm shortchanging ourselves by not trying it and maybe some day we will, but ... for now I think I'll plan a European holiday .