Yeah, how about the first time? I mean, I do not buy apps all the time, maybe once a week. And I'd have my battery dead or something like that in between those attempts.
So, I never had a chance to just hold my thumb on the home button and go my way.
I have this problem all the time. My current process is to:
1. open the App store but don't click on anything
2. hit home button
3. launch keepass client
4. navigate to apple account entry
5. copy password
6. double tap home button to bring up multitasking menu
7. tap app store
8. click install
9. paste password
It feels really stupid doing it, but you can get pretty quick at it. I can't wait for my next iPhone upgrade with touchid.
My real problem with this is writing the password with numbers, punctuation and stuff on a mobile keyboard. Feels like surgery even if I'd memorize it.
I use 1P on my laptop most of the time so it's not a huge deal. Everything else on the iPhone just remembers credentials.
I know I can force myself to use a great password for iCloud but my point is that most of the time, I'd go for an idiot password rather than forcing myself. Just like most people.
that little voice in your head that is screaming "i hate this" is your problem. It really is not a big deal to type a password, and even to type it a few times, just try to have a more zen attitude about it. It's how passwords work, stop trying to figure out how to defeat your own password, it's doing what it's supposed to do.
This may help, some special characters dump the keyboard back to the primary keyboard, so create a password that is letters, then numbers/specials, then the ' character, then more letters.
for example, pass2'word would only require you to hit the alt-keyboard switch once.