What it comes down to for us is what we can get with our money. To stay at Pop Century, we have to get a Preferred room. For the week, it is $1,200. That is 2 double beds, a mini fridge, and 1 bathroom. For that same period, we can get a 2 or 3 bedroom/ 2 bath condo at Windsor Hills for $700. There is a ton of stuff at can do at Disney World with that $500 savings. On top of that savings, we have the savings on meals. Breakfasts are easy either way. What it comes down to is dinners. We can only eat so many Disney QS meals before it is extremely old. Therefore, we are now paying $50+ each for a dinner. Even if we only eat 3 dinners at WDW, that is almost $500 by itself. Since we relax in the afternoons at the pool and room, making dinners is simple. Want a pizza? Bobboli's in the oven for 12-15 minutes. Want a steak? Throw 3 nice steaks on the grill for about $30. Want spaghetti? Noodles on and sauce simmering. Cooking for me is during the relaxing time. I can have a drink and lounge. Cleanup is easy and toss stuff in the dishwasher, turn it on, and head back to the park. Laundry is easy. Toss towels in the wash when you head out in the morning, toss them in the dryer when you get back in the afternoon. I personally hate when housekeeping comes every day. It means I have to keep the room spotless to begin with.
We are a family of 3. My DW and I cannot share a bed because it is too small. Sharing a bed with our DD is like sleeping with the Tasmanian Devil. We would have to bring an air mattress for one of us to sleep on at a Value resort. However, we now rent from DVC owners which amounts to about $100-$200 more than Pop Century. This gives a queen bed and a sleeper sofa. It will be a rare occasion where we stay onsite now unless we find a good deal.
In the end, it really comes down to what you want. If you want to stay onsite, my recommendation is to find a DVC renter. Get the points for about $12 each. For a week in a studio, you are looking at about $900. With the best rates the AS and Pop will be about $700 for a week. The $200 is worth the upgrade.