Not an Apple Jail fan myself. Although all their marketing makes the products look really enticing .... for some, especially the younger high disposable income set.
My Samsung S7 has been so good, I have never needed to change it as of yet. It does everything I need and tons of stuff I do not. I am an Electronics Engineer, and when young had to have the latest of everything electronic. Things have changed, I like to think I got smarter. When my S7 Breaks, I will get the latest no doubt, as I do when anything we own gets past it's due by date.
I wonder how many folks here think the same? Especially those who buy a car an wait till it drops before they get a new one. Are you the same with electronics? Or do you just have to have the latest iDevice.
I have an EE background. I like to have the latest if it is truly innovative and there is a clear benefit. I don't see much difference in the past three (four?) iPhone iterations. Let's face it--when it comes to phones, something personal we use everyday, even if it costs $1,000, you will likely have it for four years making the per year cost reasonable.
Not an Apple owner, prefer the flexibility and customization of Android. Apple makes great products, but like you said you have to live in their ecosystem. I often joke that about 1 billion people are walking around with essentially the same home screen icon layout on their iPhones, same notification sounds, same ringer, etc. Still, they are so good, I could own an iPhone and probably love it.
I was fine with my four year old Google Pixel 2XL phone but was planning on getting the new Google Pixel 6 Pro when it comes out next month. I do like getting the best stuff but only if it is a marked change from the predecessor.
Alas, the Pixel 6 Pro was not to be. My 2XL camera started getting flaky last month, I need a camera, I couldn't wait two months for the 6 Pro, so I ended up getting a Pixel 5a 5G phone for $449. The 5a 5G is essentially the same as my 2XL except has 5G (which I haven't used), a much bigger, longer lasting battery (which I am thrilled to have) and slightly better camera (Pixels have the best cameras, even better than Apple.)
If you like Samsung you might take a look at the S20 Fan Edition ($449). It's been out for almost a year now. I almost bought one but figured I didn't want to deal with Samsung's OS, preferring to stay with stock Android. Plus Pixel camera is better. The S20 FE has rave reviews, would be a huge step up for you and it's priced right.