DH and I started at off site resorts (late teens early 20's) , $40 a night for the Ramada, we were young and broke

and that is what we could afford (we also ate all CS too

). We used the resort to shower and sleep and that was it.
Then the value resorts had great discounts, $49 a night for FL residents so it was a no brainer, we would stay onsite. We loved it! Then if the mods had a great deal, $79-99 a night, we stayed there. Again we just used the resort to shower and sleep.
We have stayed at the Lake Buena Vista resort in DTD (the tall tower one, maybe they changed the name?) and the Double Tree with my inlaws and that was ok too but we hated the bus situation...it was horrible.
Now that we are older

we prefer to relax on our WDW vacation so a nice resort with great restaurants and a fantastic pool are right up our alley. You can really unwind at one of the quiet pools! We have tried almost all the deluxe resorts, GF and SS are the last 2 on the list. We also love having a few nice TS instead of all CS
We make more now then when we younger so we can afford to splurge a bit. We have AP's and try so hard to get great discounts. I refuse to pay over $250 a night...I just cannot justify it. We have also stayed at the Swan and Dolphin and for $125 a night it was out of this world fantastic! We do not use the
DDP....just DDE.
Now not getting a deluxe would not make me cancel a trip or anything, we have no problem staying at any of the resorts or the Swan/Dolphin. If we go for a quick weekend we do not care which type of resort we stay in but if we are going for a week we would prefer to stay deluxe.
I guess what it comes down to is who cares which level of resort you are staying at as long as you are at WDW!