Oh, dear. It does sound like you had a busy evening! I just bet that this isn't the kind of attention that Tripper likes, is it? You've probably already tried this, but will he take the pill if it's hidden in a little bite of cheese, meat, peanut butter or another yummy thing? My friend's dogs were each put on multiple meds this week and it was a zoo. She bought those little edible pill packets that they sell at the vet and now the dogs are just swallowing the pills (tucked into the packets) like treats. I don't know if that'll work for Tripper, though. I really sympathize with the eye thing! Cassie needs drops occasionally for eye irritation due to allergies. The only way we can get them in is to have my hubby hold her up high with his arms under her like a forklift (so she has no traction and can't get away) and I have to hold her head still and get the drops into her eyes (nope, the nose doesn't count...).
Otherwise it's like trying to put eye drops in a Tazmanian Devil. LOL! Yep, it really looks goofy, but it the only thing that's worked so far for Miss Cassafras. Well, it works only if you have someone around that can lift 80# of squirming doggy!
I hope that something makes it easier on you two and I can't wait to see pics of that little guy!