I'll add that when my DH and I were first married, we took a "spontaneous" trip to WDW (went over Easter--big mistake, worst crowds I've seen and we couldn't figure out why! We were young and dumb and didn't know how to plan anything). We stayed off-site in a $45/nt crap-motel in Kissimmee. We rented the smallest eco car possible. We did both WDW and USO and had a blast! We also came down with the worst flu-bug ever! I think back and wonder if we got it from that motel but who knows.
My DH and I had good jobs but we were very frugal in our mid-20s. As we have gotten older, I've become pickier about where we stay, especially when we have our kids with us. I would never think about staying in the roach-motel with my kids now. But we have definitely done our share of on and off-site stays at WDW.
I easily see the value in staying offsite, especially in the Disney Springs area. We loved staying at Wyndham Bonnet Creek condos with our kids. We've gotten to where we definitely need 2 bedrooms when we travel. So that means either getting 2 adjoining rooms at WDW, a 2-bd villa at WDW (renting points is a must if we do that route), staying off-site in a condo like WBC, or vacation home. And we've done it all. It's just how we want to vacation, how much we've budgeted for that particular vacation (we may have another big trip planned over the holidays).