After hours of research, I decided to get a Samsung Vibrant (T-Mobile version) for my wife to work on WIND.
Shortly after, I found the Vibrant can have an issue where it doesn't pick up WIND Home properly. You have to manually lock it to WIND Home, which disables WIND Away i.e. roaming.
My wife won't know how to do this, so this is a big problem.
Bell has the Vibrant. I calculated out WIND vs. Bell, and it's around $200-$300 higher at Bell depending on how long you go (1, 2 or 3 years). Not overwhelming, especially if it fixes the network problems and gives her transparent roaming when she does the occasional travelling.
But here's the kicker - the Bell version has problems too! Many Vibrant owners have complained that to keep the phone from randomly locking up several times a day, you have to lock the phone to 850 MHz only. Sounds kinda familiar, doesn't it?
Maybe Froyo fixes this, I don't know yet. Samsung took forever to push out Froyo and managed to botch their first attempt anyway, leaving few people able to test the fixes.
But what is the deal? Seriously - are all smartphones significantly flawed in some way these days? Screen problems, keyboard registration issues, network issues - is there a single Android phone out there that has not shipped with some sort of defect, limitation or flaw?
I can't remember too many things my Palm didn't do right - the occasional crash from third-party software, and one or two instances where a sync went bad and I had to manually re-categorize a bunch of memos. (I was on a plane anyway for one of them, not bad timing overall.) Hell, near the end of it's working life it even got into an endless reboot loop, again from third-party software.
But it always made calls, always connected, always got email, never (or hardly ever) froze or hung, worked with headsets fine, etc. Everything could be corrected with on-phone resets and a restore from BackupBuddy, which never failed.
Not so with Android, which lacks a solid, comprehensive backup utility. My Backup Pro is as close as I've seen so far, and it fails to restore about half the stuff correctly.
[Edit]: After consulting with WIND technical support, they confirmed the Vibrant still has the Home/Away bug. Locking the network works, but requires manual switching between Home and Away. Not great for my wife, but neither is having the phone freeze up on her five times daily.
They also explained that when using a non-WIND phone, roaming will likely not work properly. The WIND phones have settings that allow them to correctly select between WIND, Rogers, and T-Mobile (their USA roaming partner), but compatible non-WIND phones do not.
So if you take the occasional trip to the USA, you may have to manually set your phone to T-Mobile. Not hard for some, but well beyond the capabilities of many users. And something that is likely to affect all non-WIND-branded phones, not just the Vibrant.
[Edit 4-2012: My non-WIND Xperia X10i picks up T-Mobile in the USA just fine. No manual interventions required, it just works (like it should).]
Personally I'm worried about the rare situation where my wife is on a trip - road or plane - gets into trouble and her phone doesn't work because the settings are manually locked. These days, we rely on having these things more than people admit. Unless Bell has a fix for the freezing issue, I might not be buying a Vibrant after all.
[Additional]: xda-developers says that Froyo has fixed the freezing problem. I guess we'll see...