I laughed when I read your account of TH. That's what happened to Chienne & us. Crate-trained until 9 months old, then we took all three dogs on a month long road trip to visit parents.... Hasn't slept the night in her crate since. :-) Well, there's been some exceptions, but for a pretty good reason.
Unfortunately, we've had a slight downside to this. In our old place, we had a doggy door that she could go out whenever she wanted. Being the semi-nocturnal creature she was, she usually went out around 3am and then came back in. When we moved here, she would just quietly piddle on the (ancient) carpet next to the back door. She was politely not disturbing us (said with an ironic tone). Trust me, she'll let us know in the daytime when she needs out :)
I've been working on this for three years now and its pretty much solved. Now, if I could only get my husband to understand "Chiennespeak" :D
Beanie -- it really does depend on the dog for how good of a control it has and it does take time to develop...just like a human baby.
My now- deceased Yorkie actually decided one time that she was not going to piddle while we were gone and held it from when we left early at 5am until around 3am the next morning (we were on a day tour). I couldn't believe that she was that stubborn and I searched the concrete & the carpet....nada!
Chienne's part Cocker and as an adult is comfortable at being put outside around 10pm and is good until somewhere around 7am (or 8am if its raining).
Samma the terrier has an iron bladder. She'll be happy with an 9pm - 9am time period, even longer if I read in bed or go on the computer. They pretty much go out, do their business and head back to sleep until or if the sun decides to show. I have to kick them out if the weather is bad.
*** That's why I never get pulled out for walks on rainy days --- :p
I hope this helps.
toodles