Where are you going to run into any kind of 'stigma'? At the resort itself? Doubt it....everyone is in the same boat there. At a park? Why would anyone even know where you're staying. At home, when nosey nellies are asking you where you stay? Maybe. But, I'm pretty self confident....I don't really much care. I have friends that stay only at the GF...only!!! They say that if you can't stay there, you might as well stay home. Of course, these are the same people that tried to tell me that only those at the GF were able to ride in the front of the monorail (back when it was still possible), and that those at the GF had a direct monorail to Epcot! Okay, sure, if you say so.
I own DVC at both BWV and BLT. I go to WDW several times a year. I have debt. It is what it is. BUT......I stay at Pop, a lot!!! Love it there. Where was my worst stay? Polynesian!!! Man, there were some really rude and obnoxious guests there, the worst I've seen anywhere!! So, spending money doesn't mean you've got manners or class!!
The moderates? I love POR...it was my first WDW stay back when it was DxLs! And I try to stay there every few years. But, for me, the cost isn't reasonable for what I'm getting. Yes, it's themed better than Pop. And yes, the pools are nicer. And there is a table service restaurant. BUT, I seldom use the resort restaurants that I'm staying at. Hot tubs aren't my thing. The rooms are a bit bigger, but not that much. So, truly? It just isn't worth the additional cost over Pop.
And deluxe resorts? Don't get me started! I refuse to pay those nightly rates!!!! That's just ridiculous! For what? Nicer restaurants and more adult 'theming'? Nope. I can still eat at those restaurants if I want. A pool is a pool....a big old concrete hole filled with water. Sure the surrounding areas 'look nicer' but do I want to spend that money for nicer landscaping? Not really. A gym? Sure, people use the gym at WDW...but truly? Not all that many!
Long story short? Stay where you want. Pay what you want. If paying upwards of $400 a night floats your boat, have at it. None of my business. I have never, ever felt like a second class citizen when staying at Pop, but of course, I don't feel like an upper crust person when I'm at BWV either!!!!