B.B.
I agree it's just part of the process. It's good that he's trying so hard!! My ODS went back and forth so much. He wanted to be in underwear, but he sometimes got too busy and forgot to tell me he had to go. I didn't push him, and if he had an off week, we would take a short break and try again. He wasn't truly ready until he turned 3, though. It finally clicked with him. He was day trained within 3 days, and night trained in another week.
Here are some awesome cloth trainers, I told him they were special underwear (if he thought they were anything similar to a diaper he would have peed in them). http://hyenacart.com/ladderhilldesign/ I got the snap trainer, but she also makes pocket trainers (you add an insert in the pocket for absorbancy) that just pull up/down like underwear. You could even have him help pick out which ones he wants. She will also make customs, I believe, just email her and ask. ODS wore these while out of the house, and undies at home (since we were always close to a toilet). He still likes to wear them if he sees them, just b/c he likes them! They are super soft on the inside!!!!!