It is tricky if you don't know if you want to reconcile. If you were committed, I'd say he probably shouldn't take the condo, but if you aren't sure, I would not use it as a litmus test of any type. You said yourself he loved the spot, and it makes him happy. So, if he is faced with possibly a life without you, then why wouldn't he want to start from a place he feels good about?
Also, could you not see it as a positive sign, if you all were happy there? I bet the connections you are having to it that are negative, he doesn't feel at all. In fact, I'd bet on it. I'd ask him. I can personally associate 100,000 things with the AP, that my H does not.
I think this is a chance to talk thoroughly and non-defensively about something. Also, I think if you are "waiting to feel safe" that this isn't going to happen without some risk taking, and some MC.