I read negative reviews about the bussing at POR. Makes me nervous. The bonus is the boat to DTD at POR.
We just faced a similar choice for our trip in September. After always staying at WL and loving it, we gave POR a try.
In our opinion, we would probably say WL Std View is worth the $350 more, but whether it is for you depends on a few factors:
1. Your tolerance for bus crowds. In our experience the bus ride times from POR were only slightly longer (if at all) than the times from WL at the same time of year. Overall the bus experience isn't great either way because WL buses often have to stop at GF or FW on the way to parks. POR buses have four internal bus stops, and sometimes share with POFQ. For us the big difference was the crowded feel on the POR buses because they often arrived nearly full, which does not happen nearly as much at WL.
2. Your park preference. WL is more convenient for MK due to the boats and very quick buses. WL might be less convenient for Epcot since the bus ride takes a while and the monorail involves a boat to CR and two monorails. (But is more fun...)
3. Your frequency of visiting DTD. The boat from POR is great. But does take about 25 minutes. Still it is way faster and more relaxing than the often long bus ride to DTD from WL. I would strongly consider POR if DTD was a priority.
4. Your enjoyment of other deluxe amenities. For us, we missed the balconies that WL has, and the fact it is all under one roof, which is great in bad weather.
For us the rooms were very comparable on the inside, but we had an Alligator Bayou room at POR, so it didn't have the dresser we were used to at WL. The Royal Room would have one, and the fancy decor as well, which might appeal to young princesses. We instead chose a preferred room at POR to minimize the walk to the lobby and bus stop, which worked out great for us.
Either way you will have a great trip, and during your trip it would be fun to take the time to visit the other resort. They both have their unique advantages and are nice to visit.