My first smartphone was the HTC Touch Pro (I still have it) that I got in 2009. At the time, while I was using Macs, I was not an iPhone person. I can remember being able to cut and paste and send MMS with my Touch Pro, yet friends on AT&T were not able to do so on their iPhone of the time.
I hated the look of the iPhone 4 and 4s (but I own both now) so I waited until the launch of the iPhone 5 on Sprint to get my first fully purchased new iPhone. I was unwilling to switch to AT&T just for the privilege of using the iPhone.
I chose to switch to iPhone in 2012 because (to me) the Apple ecosystem had matured enough. Unfortunately for me, Apple chose that year to abandon PowerPC Macs for use with the iPhone.
To prepare myself for my new iPhone 5 and iOS, I used a gifted 3GS from Christmas 2011 to September 2012 as a secondary phone. I used the 3GS on WiFi and at the time Talkatone would let you use a Google Voice number free (with ads) for calls and texts. So, the 3GS was capable of everything when on WiFi.
The 3GS introduced me to iOS and jailbreaking. I made all my jailbreaking newbie mistakes on the 3GS where it didn't matter. By the time I got the Sprint iPhone 5 in 2012, I was prepared. I jailbroke my 5 in 2013 and every iPhone I've had since, with the exception of my current 11 Pro Max, has been jailbroken. I enjoyed having a lot of the things that have come around just recently to iOS long before now.
Apple's abandonment of PowerPC forced me to create my own methods of syncing with my device and using my device. I do not now use the Apple ecosystem (with certain exceptions) because Apple never allowed me in to begin with. All my workarounds (jailbreaking, third party services) became a habit and I don't need Apple to use them on my iPhone.
My favorite iPhone is still the iPhone 5. If Apple could make the iPhone 5 in the size of the Pro Max with modern iOS, I'd be very happy.
Phones I have: HTC Touch Pro, iPhone 3GS, iPhone 4, iPhone 4s, iPhone 5, iPhone 6 Plus, iPhone 6s Plus, Pixel 3a XL and my current phone the 11 Pro Max. The 3GS, 4 and 4s I acquired. They were never used as primary phones.
I'd just add that I also have my 2007 Sanyo Katana flip phone in the garage. Doesn't work anymore, but I have it.