I was going to post on your last thread but it locked!! That last phone call sounded really good, I don't think the 'negatives' you posted were as negative as you thought (sorry not to validate here ) and also, doesn't it go to show, that even when you are not feeling tip top you can still call him and have a positive interaction where he stated that he would like to hear from you again soon. I would be encouraged by that.
I see no reason not to optimise your chances of seeing him by going when you know he will be around. I think that he feels more comfortable around you, more so than the summer as you have had such long, interesting and fun phone calls. I think at this stage he may be scared if he knows you are going specifically to see him as he may think there is a r talk on the way. However if you are casually going up there anyway and he happens to be around and then you have a super fun evening and a r talk naturally happens then that is no big deal. Ok, my ideal T scenario... I had in my head a snowy forest, lit with fairy lights scene where he declares he has been a fool and you are the best girl in the world. Are there many fairy lit, snowy forests in NY?? Maybe that is why he needs a beard? To keep his chin warm.
My DBing advice is to play it light and have no expectations. Plant some more seeds T...
How about a quick email saying something like
'Hi B, I am going to be in NY sometime in December or January. Dates have yet to be confirmed but I thought, as I am there, perhaps you would like to meet up (or maybe... wondered if you were doing any gigs around that time or something). T'
Something like that - reading back it is a bit rubbish but maybe it might give you some ideas?? I would do it sooner rather than later as it is already December - eeek, I really have to start my Christmas shopping soon!