The timing is a PITA for sure. I give Tin his meds at 7am, breakfast at 8 then dinner at 4pm and meds at 7pm......usually. Problem is that if I am out or get invited to dinner then giving him his meds is difficult as he won't take them from our helper. If they are late then I try to move it back slowly over the next few days. I can see how my scheduale wouldn't work well for you as you would be at work still when dinner would be served.
My mom was hypothyroid as well and she was terrible about trying to stay on a schedule for her 1 pill/day. After seeing what it did to her we do our best to have hubby and dog take their pills as prescribed but it is soooooo much more difficult with the dog as his are twice daily. All we can do is the best we can and it sounds like you are.