tl;dr possibly switching; definitely buying some new flagship off-contract this December so I can keep options open.
I'm going to have a very, very tough decision when the 2 year contract on my Lumia 920 expires in November. Microsoft won me over with their fresh approach (Metro UI, hubs, tiles) and the promise of integration across phone, tablet, pc and TV. I happily gave up my iPhone 4 and any thoughts of an iPad. But two years into WP, and three months into Windows 8.1 (with a Dell Venue 8 Pro) I'm starting to feel like a second-class digital citizen. As much as I love my 920, I want something lighter and with a much faster camera. The DV8Pro is a great value, but the low-resolution screen is getting old- as is the lack of apps, and the occasional hassle of dealing with and "managing" full Windows. I'm tired of bugging companies to release apps on these platforms. I'm tired of Microsoft not making more of an effort. I felt a little better after /BUILD and after getting WP8.1, but having seen the recent Apple and Google conferences I feel like Microsoft continues to fall farther behind with each passing season. We're now waiting for Threshold in mid-2015 to solidify the Windows phone/tablet situation, which means another 12-18 months of treading water (during which time we'll see another rev of iOS and Android, and Apple and Google likely go even further in the TV, automobile and wearables spaces). Oh, and just six months from now Nokia will be free to re-enter the smartphone business. The more I think about it, the more I wonder if there is any way I *wouldn't* switch this winter. I don't know, maybe my love of metro and the promise of what could be will keep me on board a little longer. Either way, I'm not signing another two year contract. I'll get some new flagship off-contract, and probably a new tablet in the spring. If I had to guess, I'll be looking at an iPhone 6 and an iPad; at least they'll hold their resale value for a while in case I decide to change again.