I spoke to the sheltie rescue...Long Post
The lady that I spoke to about Toby was very nice, but I left the conversation feeling a bit frustrated.
Through no fault of hers, I felt kind of put on the spot and despite everything I've been through with Toby, couldn't give her any good examples that REALLY described his behavior. I felt like I couldn't really make her understand just how anxious he was and how much it affected his life, I just made him sound like a regular sheltie that barks at sounds or tries to chase traffic. I felt like i was having a complete and total
BRAIN FART. 
I emailed her some info today that should clear things up for her.
She reiterated a few times that the dogs they've had who did require anxiety medication were able to come off of it eventually, but that Toby could be the exception, that 1 in 300 dog that needs to be on it for life.
The more I think about it, the more I think that maybe Toby would do better with a family in a rural area. I don't think while he's living with us that he'll ever be able to come off of his medication, but that may be possible if he's in a different environment. This makes me wonder if she might suggest to other members of the rescue that Toby be taken out of our home for his own well being.

Please understand, nothing was said to me about taking Toby out of our home, this is just a conclusion I'm coming to again on my own. I really want what's best for him.
Anyway, at the same time she was very supportive, should Toby need to remain on medication and told me that my vet is COMPLETELY off base about the online pharmacy I tried to get his medication from. She said that the rescue uses them regularly. This made me feel MUCH better, my vet made me feel like I'd totally lost my mind.
The sheltie rescue lady also agreed with me, that my vet seems a little out of her element and that I should probably seek a vet with more experience with long term anxiety treatments. She thinks that the vet in the US is a great idea and encouraged me to call them to verify that the vets there do have experience dealing with long term anxiety in dogs.
The sheltie rescue lady also encouraged me to talk to the behaviorist again that saw Toby before and maybe have her come out to the house again at some point. I've actually signed up for a reactive dog seminar with her this weekend so I'll definitely talk to her. The rescue lady may come to the seminar with me, which I'd love!
The sheltie rescue lady is someone who's dealt with anxious dogs before, and she indicated that in her experience she's had little to no luck with natural treatments for anxiety. That being said, she didn't discourage me from seeing the homeopath either so I'm still going to give her a try. The homeopath has been in contact with me and is very enthusiastic about treating Toby and has been great about trying to work with my schedule.
Enough for now...