I might miss a few, but here goes, with commentaries:
WinMo:
HTC TouchPro2 (My first smartphone and last Windows phone, do like some of the PocketPC features though. $350 on Sprint contract, a choice I regretted later when I realized the cheaper HTC Hero was so much better. This was my last time I was on contract as well, after that it's all prepay.)
Symbian:
Nokia N97 (bad, couldn't get used to Symbian interface)
Maemo:
Nokia N900 (one of the best smartphone I ever owned, a true linux device, very durable too. True stereo speakers, Carl Zeiss lens, dual LED flash, 32GB internal storage and microSD slot, support Adobe Flash, offline Maps, that gives the Nexus 5 a run for it's money while being 4 years older.)
Android:
LG Optimus M
Samsung Indulge
Motorola Triumph
Samsung Galaxy S 4G (This one is different from the original Galaxy S despite appareance, not as supported by roms devs, not recommedend.)
Samsung Nexus S (Absolutely horrible camera, not the same as in the Galaxy S. I like the curveness of it though.)
HTC EVO 4G (and Design shortly) (Made me realized what a pain it is to bootloader unlock (losing warranty through HTCDev) and root HTC phones, hence the reason why I don't buy their phones. Also I don't like how bloated Sense is/was.)
Samsung Galaxy S II T-Mobile - (Disappointing compared to the unlocked version, its CPU though clocked faster, performed slower. Lacks Wolfson DAC so not good audio quality.)
Samsung Galaxy S II (Excellent, a milestone for me, huge increase in hardware. From this device onward I only buy sim unlocked phones or carrier branded phones I can unlock, and only GSM phones onward.)
Samsung Galaxy Note N7000 (Paid $850 to import, most money I ever spent on a phone. Excellent device, very durable despite large size, can't say the same for Samsung phones today.)
Samsung Galaxy Nexus (Correct me if I'm wrong, but I think it was the first Android phone with 720p screen, great phone, re-bought it twice, but its base on luck whether you get one with a good screen or doesn't have heat issues.)
Samsung Galaxy S3 (Excellent device, but disappointed with build quality, this caused me to lose interest in Samsung, for now.)
Nexus 4 (Love this phone, I like the way its built more than the N5 so I'm keeping it for now. However, 16gb storage space is killing me. Paid $250 for it so I'm completely spoiled by the price when considering new phones now.)
iPhones:
(Never bought one, though my family members uses it, but it never gave me real incentives to own one. Sorry just had to mention it.)
Xperia Play (all three versions; ATT, Verizon and Unlocked)
(2nd fav Android device of all time, it's the only one with a gamepad, unfortunately the hardware was outdated even on release date. My biggest Android wish is for Sony to release a second one. As long as it gets decent hardware, I don't care if it have bloated UI (which imo Sony UI is), locked bootlader, no updates, I would probably still buy it for the gamepad.)
Samsung Galaxy S / Vibrant / Captivate
(My fav phone of all time, owned a handful from different variants, but they are all quite similar, unfortunately sold or gave them away. Very compact, easy to sim unlock with root, MicroSD slot, very durable screen with good AMOLED screen quality for its time, still supported by devs to run KitKat even today, excellent Wolfson DAC audio quality, still to this day the highest quality sounding Android phone I used (with VooDoo-supported kernel to improve the audio), even better than the Galaxy S3 also with Wolfson DAC, S4 use a high quality Wolfson DAC as well, but auto upsample music to 48khz. Beside the screen, parts are cheap and easy to replace too.
Two mayor flaws with the Galaxy S. The atrocious GPS signal, there are software and hardware fixes you can do, but don't even depend on it for navigation. And no front camera for Captivate and Vibrant variant (the Canadian Bell's Vibrant have one though, but never owned it.) Not aware of any version that have LED flash either.
In the past the older CM roms for these phones had issues causing it to fail to dial 911, this issue have been fixed with latest version.)
I have rooted every single Android I ever owned. I did not 'know' about Android first, I heard about "rooting" and that led me to getting an Android phone to root it and learning about Android afterward. I have never bricked one to the point that I can't unbrick it myself either. I also don't think I ever hated any Android phones I owned, some had really disappointing aspects that I dislike, but overall I have great experiences with the freedom and customization Android allows.