This is sad, bc it seems like his current owners don't care too much - nor do they care for his safety...an outside dog??? In that pic he doesn't look 1.5 pounds, do you think?
I would ask:
**How did you house him outside? (as if you're just wondering, like you may want an outside option - but really, this is just so you can get more background info on the fella)
**What does HE mean by not "socialized" - it may not mean what it means to you/us.
**Be very open-ended - "tell me about his training" - if there's just a big "uuuhhh" after that, you have some bargaining room there.
**What does he eat? Where does he sleep? Does he go for walks?
**Do you have his vet/medical history?
I think questions like this might help fill out the picture of this little fella. He should take less for him. I would be straight up and say something like "well, I just don't know what to do. Puppies go for the same price you're asking - and your guy is going to take more work since he'll be switching homes and isn't yet trained or socialilzed. Tell you what, I'd like to offer $300 (?) - why don't you think about it and let me know in a day?"
I hope you take him, it is obvious you would give him SUCH a good home - your big heart comes across as you write of him. But if the timing isn't right, I'm sure he'll find a good place - and you'll be a future mom to another pup!
Keep us posted!!!