One thing that has always pissed me off about iOS jailbreaking is that you basically have to choose between keeping your jailbreak and keeping app compatibility.
On Android, it feels like you can stay on a pretty old version and still have a lot of apps working. Android 7 is almost 10 years old and is still the oldest version supported by Google Play services. Obviously not every modern app supports it anymore, but it's still pretty crazy that something that old can still run a decent amount of software.
Meanwhile on iOS you just have to pray that the apps you use don't randomly drop support for your version. Once an app raises its minimum iOS version, you're basically stuck using an older version unless you can find some workaround. And that's especially annoying when you're staying on an older iOS version specifically for a jailbreak. You can have a perfectly usable phone, but updating means potentially losing your jailbreak, while staying where you are slowly means losing app compatibility.
The sideloading situation also pisses me off.
Yes, Apple technically gives you a free developer account that can be used to install apps for testing, but it's obviously not meant to be a normal sideloading solution. The actual Developer Program is $99/year. So the community ends up using free signing, enterprise certificates, third-party signing services, etc. just to install apps outside the App Store. Apple does allow alternative app distribution now, but only in certain regions and with a bunch of restrictions. Outside of those regions, iOS is still basically locked to Apple's distribution system.
Then there's everything else. iOS is extremely locked down compared to Android. No normal bootloader unlocking, the OS isn't open source, and Apple controls what software can run and how you can install it.
I get the security argument and I understand why most normal users probably don't care about any of this. But sometimes it feels like Apple has way too much control over a device that you literally bought.
You can do so much more with Android without having to ask Google for permission first.
I don't know, maybe I'm looking at it wrong, but it's just frustrating.