Is there ever going to be a time when I can leave Huckabee (19 months) alone in the backyard? He pulls plants, digs etc? He is not my first lab but he is by far the most head strong.
I would have thought you could have done it by now. Do you mean just let him out in the back garden for a few minutes or do you mean shutting him out there? If he is out there on his own for some time, he will look for mischief!
My pup is 22 months and I think she would be fine out the back on her own without wreaking havoc, but her issue is alert barking. She does it less than she did but I wouldn't want her scared out there or annoying the neighbours so I wouldn't yet leave her out there (I'm talking for couple of hours or so). Perhaps one day. But it does sound like your boy might still get up to mischief if you left him for a length of time.
Our two Labs have the run of the house and the backyard, 24/7 since we have a dog door. For us and for them it works fine. We have a next-door-neighbor with a friendly pit that often barks, but Cooper seldom barks back. She only rarely barks when in the back yard. Neither of them are escape artists. On the other hand we have two friends with Sammies, that can't ever be in the yard unsupervised, because they bark at any other dog that is on the other side any fence.
When she hears a noise that startles her or sees something or someone which/who raises her hackles and makes her alert to possible danger.