This isn't a matter of nice or not nice. This is a matter of whether or not he sounds like he's doing his job or not. Let's see if I get this straight:
1) You were told you would be put in for the May boards; you weren't.
2) You were not put in for the next boards: June.
3) Your OR could not remember who you were or what you applied for.
4) You went to MEPs and therefore already knew you had to have a waiver, which you applied for, yet your OR said you needed one after the fact (the implication here is that the OR didn't realise you already were waiting on said waiver, which shows disorganisation).
5) You went up for the July Intel and Suppo boards and already know you are a non-select for Intel (wait, what? It's only half way through July, you couldn't have July results already...)
6) Your OR excused himself from the conversation before you were satisfied you had all the answers.
7) You have no idea what programs you're actually even being seen by boards for.
Three questions I have are:
1) Something is definitely fishy here; is there anything you've left out?
2) How many times have YOU taken the initiative to call, email, show up in the office, be a squeaky wheel? If you're not a high profile candidate and show how much you want it, while other candidates are doing so, you will receive less attention.
3) Have you tried to sit down with the OR, figuratively or literally, and dispassionately ask the tough questions?
If you haven't done 2 or 3, you need to before you place all the blame on him. If you've done 2 and it just isn't working, you need to do 3 before trying anything else. If you've done 3, time to call your Officer Programs Officer, and dispassionately direct those tough questions to him or her.
After that point, we can discuss the issue more in detail, but I'd prefer to do it over PM somehow (maybe I can send you a PM with my email address?), because I might have to get CRUITCOM people involved. It probably WON'T come to that though, and we should try very hard to make sure it doesn't. Jumping the CoC is never a good idea.