Well, I've only seriously planned our current trip, but we went through a few stages:
(1) price -- our budget can stretch only so far without us cutting out other things or shifting priorities which don't suit us
(2) amenities -- we felt it important to have a sit down restaurant, a quieter/less pop-culture kind of feel, and a fridge. We wanted non-bus transportation, but it wasn't a must since we're driving down anyway.
(3) what ifs -- related to the price; how would we feel if we stayed at a monorail resort and didn't feel it justified the "double the cost" price of the moderate? how would we feel if we booked a value and got annoyed at the lack of a sit down restaurant or long bus waits or whatever else the values are "famous" for
I do believe our trip would be easier if we were at WL or a monorail resort, but we couldn't stretch that far for our family *and* ask extended family to do the same. So, balancing all of the above, we chose a moderate.
We then narrowed down the choices -- no CBR b/c DH doens't like the beach, and points for CSR because of the exercise room (for coach/athlete BIL) and high speed internet access (both DH and BIL are self employed and may need to check in on clients, which would pay for the internet connection as a tax write off pretty quickly).
We'd have done PO-R if our extended family had opted to share one room (with trundle) instead of two separate rooms.
I think if this trip goes well, the Hypothetical Future Trip will include a stay at CR, 'cause Dh and I have fond childhood memories of thinking that place was so cool and we both appreciate the combination of architecture, technology and public transit

If our budget didn't extend to CR the whole time, we'd probably do WL too....but I don't expect another WDW trip for a couple of years, so who knows what new factors will come into play?
