The fear here (which isn't really detailed in the post because the OP has some experience in this area) is always going to be that you will say the wrong thing and somehow disadvantage yourself. If the respondent goes along and is willing to cooperate that won't happen. But if they don't there may be some nuggets in whatever you say that will come back to haunt you (just like talking to the police w/o an attorney might).
Content? User accounts? For a private site behind a login screen, how would they even know whether the service your trademark is being registered for even does what you say?
Trademarks can be a bet-the-business problem. Best to see a trademark lawyer. Shop around, there are lots. I prefer small law firms as you have a better chance of getting personal attention from a principal.
However the law is, as my favourite legal blogger says, "a broadsword, not a scalpel".
Well obviously not in this instance.