A user like you strikes me as someone who might like Android, ever give it a shot?
yes my role requires this. I have htc flyer 32GB t-mobile, huawei s7(gsm/hspa), galaxy tab 7 3G Verizon, ipad,iphone.
Android feels hacked together - tablet specific apps not good at this point. Honeycomb works great on the HTC flyer (single core @1.7ghz) - but i actually downgraded back to 2.3.4 gingerbread because the lack of apps and some apps not working with 3.2 honeycomb did not make it a great upgrade.
The ios environment is definitely more strict but at the same time - everything is more organized. CYDIA and one other repo are managed extremely well - android has no direct equivalent as far as being managed. Bad item on a repo? gone in an hour. this does not happen with android.
webos is somewhere in between - but obviously is dead in the water as far as developers are concerned.
X86 ports to android and ARM ports to windows will be interesting and if wp7 wasn't so dead i might give it a try.
Apple doesn't have a huge sell for me on upgrading this time. The baseband and A5 are both much more protected and check each other - OTA upgrades will allow apple to nuke jailbroken devices far easier.
I like the fact the 2008 model device is running current o/s level 4 and many apps are still compatible with ios level 3 - so that original iphone - i can find tons of kids apps and donate them and that old armv6 will run just fine. REPO's for IOS are aware of 3g/3gs/4/ipad/ipad2 capabilities and provide you with the right stuff. IPAD specific apps are plenty and there are hacks to make iphone 4 apps (close in resolution) run natively rather than downsizing to 320x480 and stretching (cydia app).
Honestly until the networks can stabilize on a faster protocol for the same price - i don't really see the need for a faster phone. I get 5 meg down with the 3G service now unlimited (mostly) on ipad1/iphone4 - and things render just fine and apps work snappy. I don't game really. I guess when verizon/sprint/at&t give us unlimited LTE speeds of 10/20/40 meg with no overages - then i would see the need for more power.
But i have my macbook air - pdanet tethering to ipad is solid. paid $500 for the air and it does everything the ipad1/iphone doesn't. so i'm not sure i want to spend another $500 to early upgrade to slightly better screen/cpu/ram?