Ohh no, poor Chloe.
As far as trying to get the pills down Chloe's throat, have you tried the Pill Pockets? They have different sizes, as to accommodate large or small pills and Beckham LOVES them. He will eat anything if it's wrapped with a pill pocket.
As far as the sore goes.... Beckham has the same thing going on. It started out as what looked like a zit on his chest (white head and everything). Then it got bigger and more gross looking. We thought his harness was rubbing and making it worse, so tried a different harness. But the sore was still there.
I asked my puppy class teacher, who is also a vet. She said it was most likely a benign cyst that are very common to boxers. They start out looking like zits and then get progressively worse and can get to the size of a dime. She said they will run their course and in a month or so will scab up and go away.
Beckham's is at that point now and it doesn't look pretty. She said if Beckham was getting neutered soon, we could have it cut off or biopsied. But just to keep an eye on it and if it doesn't get larger than a dime or look like it's filled with pus, it should just go away on it's own.
I'll try to get a picture of B's sore and post it.
Sorry for the novel response... Hope this helps a bit.