Hi TAS,
Correct me if I'm wrong, but I think I read another post by you where you talked about long term abuse as a child? People who have suffered that like us, often have a lot of trouble with boundaries, especially in the area of being really scared to run into one. Because we often were not allowed to have any of our own and running into our abuser's would get us hurt.
The truth is that a boundary is just a demarcation of where your stuff ends and another person begins. There is NOTHING wrong with running into someone else's boundary. It's theirs, says nothing about you, and is really only about them. Since our boundaries are our own, its also our responsibility to make them known so by definition, you may not necessarily know someone else's boundaries beforehand. Problematic behavior occurs when the boundary is made clear to you, but you refuse to respect (which you have NOT done).
I think your T sending you the text "I am now officially on vacation" was because since he had just sent you a text, he was probably worried that if you sent another and he didn't answer, that you might think you had done something wrong, so he wanted you to understand beforehand that there would be no response, so you wouldn't be guessing the reason. So I don't think it was a matter of thinking you wouldn't respect his boundary, it was just clear communciation to save you any possible angst.
Same thing with the check. That is his boundary that he will inform you ahead of time if he needs to be compensated for his time. When he gets paid and for what, is his decision and he has now made it clear that he is capable of communicating that to you; therefore, you can relax and not worry about "is this ok? should I be paying him?" because he'll let you know.
In both these situations you are not in trouble, you have not done anything wrong, it's just about being clear and communicating.
I have run into my Ts boundaries a few times and remember really panicking once. My T has a typo in HIS NAME on his Iphone, so whenever he sends an email from there, his last name is misspelled. I am a technical writer and this DRIVES ME BONKERS! It's like I have this itch I can't scratch every time I see it. So I had emailed him and told him about it and nothing changed. Finally I couldn't take it anymore and asked him in an email if I could change it for him. He emailed me back (we had been rescheduling an appointment) and said he'd be more comfortable changing it himself and if that was creepy we could discuss it at our next session. I think he started counting backwards from 10 when he hit the send button because that's how long it took me to make an emergency call. On a rational level, I got that he used the word creepy about him saying that, but on a visceral level what I heard was "wow, you're REALLY creepy wanting to change my phone." I was in complete meltdown convinced I had done something REALLY wrong, that I was going to be in a whole bunch of trouble and that I may have possibly damaged the relationship beyond repair. In retrospect, I may have overreacted.
He called me back and I freaked and apologized and explained. When I finally ran down, he told me I had done nothing wrong. That it was not inappropriate of me to ask and even if it had been, he would have handled that and it would have been ok. That he simply felt more comfortable changing it himself. That he had started to worry about telling me no (one of his exceedingly rare confessions of counter-transference) but realized that was wrong, that I could handle hearing it. That we were fine. That it was his boundary and said things about him but nothing about me. And that I wasn't supposed to know where the boundaries were ahead of time. He also apologized for using the word "creepy" that he had been in a rush and it was a poor choice. It really helped me to see that running into a boundary was not the horrific, terrifying act I had always thought it was.
Hope that helps.
AG