Food for thought, validate but do not give him a definite answer on anything unless it is something that you know you ca live with. Do not have him put you on the spot to make an immediate decision about anything. You can respond with "Hmmm...you've made a great point, let me sleep on it and give it some more thought before I answer you." One your validating and you're also setting a boundary to let him knwo that he's not going to push you into anything that you do not want to do.
Personally, I'd play it by ear, if things are going well then perhaps say the I miss you. I actually would avoid it all. This is a finance discussion, saying you miss him, really is bringing up R talk. He may just turn on you. Play it by ear and get a feel for where he is leading the conversation.
