We make a lot of trips to Disney (roughly 6 trips per years since 1998). We have stayed in all three All Stars more than once, all four moderates more than once, and several deluxe resorts (Contemporary, Poly, Swan, Dolphin, Animal Kingdom Lodge, and Yacht Club). I can honestly say that we have enjoyed each and every resort we have stayed in.
Living in Tampa, we take several short weekend trips each year, sometimes going over Friday after work and sometimes arriving Saturday afternoon for a quick trip. More times than not, we stay in a value resort. The prices are just too good to pass up and we really do enjoy them. We will upgrade to a deluxe if we are going for a relaxing, do nothing, maybe only go into the park for dinner typer of weekend.
If we are going to be there more than three or more nights, we usually opt for a moderate because the prices are in the middle so we don't are breaking the bank to stay there and they offer more amenities such as larger and more pool options, bike rides and boating. If we are going to be there that length of time, the chances are good that we are going to spend a good amount of time resting in the resort.
I hope this helps.