It depends on the latest offerings by the companies making the hardware. If they finally stop dabbling with stock Android, and release all the kernels and things to make the community hack it, than I'd buy another hands down. If they refuse to update the next phone, then I'm in a worse boat than those Apple kids, and would probably wish to stay in the comforting walled garden of either an iPhone or a Windows phone.
I think we should all look at the original Samsung i7500,Motorola Dext/Cliq/Backflip owners as reference.
The Samsung i7500 Galaxy owners have been left in the cold. Still running Android 1.5, many bugs still un-address. Moto Cliq owners are being promised 2.1. Meanwhile, new android phones are coming out at a rapid pace. 6-8 months of waiting for an update is like an eternity. My wife has a backflip (free phone replacement when she lost her iPhone) and she has no Kindle, no google nav, the phone has better specs and a faster processor than her old iPhone 3G but it is dog slow due to the fact it is running Android 1.5. It currently sits in the closet; awaiting for the update. We just keep the phone around because it is GSM and we can unlock it for international travel. We will wait till 2.1 comes out for it. She is back to using her old Windows Mobile phone (for GPS) and is waiting for the "white iPhone 4"
Sure, custom roms are nice but where are the custom roms for these phones I've mentioned. Also, suppose you can shoe-horn the latest "xda-hacked" Android OS on the phone, what about the proprietary drivers? The Galaxy S has a gyroscope. Suppose you can get Android 3.0 on it but have no drivers for the gyroscope and your wifi no longer works because it is not an official ROM. Furthermore, your cellular signal is degraded because you are running a generic baseband radio and not the one shipped with your 2.1 OS.
Then Samsung comes out with the 3rd gen Galaxy, say, the Galaxy Ultra that has 3.0, supports gyroscope, and adds cool stuff like USB OTG, and some other cool features in December. Wouldn't you get pissed off?
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