I really had this whole plan in my head of having him on a super tight schedule, but Truman had different plan in his! I think we're going to continue free-feeding for now, as long as he doesn't get carried away. I know that being overweight is harder on older dogs, but he doesn't seem to be a piggie.
As far as the grass thing goes, I guess I can tread lightly. I think he'll soon realize that it isn't so bad.
Thanks for your ears, guys. We're both learning as we go!