I'm a big fan of preventing problems by crating. Ollie was crated until he was close to 3 (he'd tear stuff up otherwise), Finn was crated until he was about 18 mo., and Lilly is 4 and still gets crated most of the time we're gone. Each dog is different. Don't feel bad about restricting his freedom, then working more space and time out back in. I would definitely try Jeff's idea and think about building up the time he's out, too. Basically, just start over with out-of-crate training.
One thing to consider is that dogs fed on a schedule will generally have to poop on schedule, too. Try adjusting his meals so that he gets a smaller meal at night so he has less available to poop out during the day (and thus relieve some of the urgency, if that is indeed an issue) and possibly tweaking the time he's eating -- might be earlier; might be later. Kibble's transit time is generally around 12 hours. Sometimes adding or subtracting foods from the diet can help. I know that with Finn, the only one of ours who will sometimes poop in the house, if we feed him too early in the evening, then his timing is off. Same for if he gets more organ meat -- he'll have to poop sooner.
Try walking him in the morning before work to help him eliminate. Exercise always does it for my dogs!
Let us know how things go!
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