I started using Android from the G1, and was a massive fun of customising my phone with custom ROMS, etc. I eventually switched to iPhone and whilst I have jailbroken my phone before, I reverted it when I realised I didn't have much reason to need a jailbreak on my phone. I would still love the ability to sideload, but if that's my tradeoff for not using Google I'll take it.

Carrying a cable has never personally been a problem for me but again, it depends on a few factors (most of my company uses Macs, with cables required for the keyboard and mouse so there's always one laying around).

I personally use an iPod Video for music, as I prefer to either download my music from Bandcamp or buy and rip CDs. I find it a much nicer experience. I do carry the dongle around in my backpack on the rare occasion I need it, but my headphones are bluetooth (although I really only use the 35mm jack).

Repairability is not an issue at all, as far as I'm concerned. I've replaced personally the screen, charging port and battery and it probably took all of an hour to do. Buying the parts was easy and quite cheap, and fitting was a breeze thanks for iFixit.

Also, you're only locked in if you choose to me. The only things I have synced to iCloud are my contacts (also backed up via CalDav to my email provider) and Photos (backed up on my home network). Admittedly I'd have to buy apps again if I moved to a new platform, but that's the case with Android too.