Okay, I'll bite...
I have stayed on and offsite many times at WDW, Uni and offsite. I agree WDW prices are a bit crazy, and as someone else said, 3-beds doesn't fit the WDW room plan.
One reason to stay different places is variety.
I really like the Uni hotels. I've never stayed at C Bay. but have enjoyed Porto, HRH, Aventura, and Sapphire Falls. At WDW, I have stayed at just about al of them, except the purely DVC hotels. I've also stayed at the Swan/ Dolphin, and many offsite places a number of times.
In the before times, a practical consideration/benefit of any hotel was the amount of time it took to get from our room to the park, especially in the morning when every minute counted. When I say this, I mean the total time, not just the drive time. One of the downsides of the WDW moderate hotels is the amount of time it takes to walk from your room to the food court. Sometimes the offsite options are actually great. I also often took advantage of all the peripheral park hours - am and PM- so being able to walk to my hotel room at the end of the night was also a plus at both WDW and Universal.
A second factor for me is how fun each hotel is, namely the pool. At home, I have seasonal access to basic pool for a nominal fee, so a fun pool is a feature that often matters to me when I'm vacationing. It isn't important for short and winter visits. Overall, I like the pools at the Universal hotels, but they don't have water slides. A plus of the HRH was the live poolside musicians. A downside of HRH and some if the WDW/offsite hotels is the noxious fragrance they spray everywhere. The WDW value hotel pools are also just so-so: no water slide or hot tub. The WDW moderate hotels have great pools. Some offsite pools are great, others are beyond dull.
In the before times...another consideration is the hotel breakfast options. Mostly, how quick are they? Mostly, aside from Mickey waffles, and decent coffee, breakfast food is fairly standard. As long as a place offers quick access to the basics, including some fruit, I'm not very picky. What I don't want to do though is wait in a 20minute line, or spend 10 minutes hunting for a table. Also, I'm not picky about décor, but CLEAN is important.
I also really like a few other basic amenities: a nightlight, a vanity/shave mirror, light, plenty of electric outlets, and plenty of counter/desk space. Oh, and I'm not too picky, but I need to be able to shower. (adequate water flow, no sudden temp changes, towels, and a shelf for my shampoo/soap. )
I think one reasons people stay onsite is more just habit than anything else. At one point, WDW offered deals and pricing that made staying onsite worthwhile, and some folks just like to return to something familiar. They look forward to seeing giraffes, talking to their favorite staff members, and eating at the Pop food court, so they return to the same place.
Lots of folks think it is crazy to return to WDW year after year.