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?
So if you file 1b (intent) that is fine but then you have to pay a fee and do another filing (iirc $100 more) when you finally use the trademark. And wait for approval. So if you can start to use it (in the class you have filed in) right away that is the cheaper route. Generally this is stuff that lawyers have little benefit in telling you since they get extra money for doing the extra work for you. And of course it is probably more ritualistically or legally correct. But if you are going to be lean you will have to cut corners and take some nominal chances. Important point.
Or operate the site that they see at something like
joeblow.mydomain.com instead of "www.mydomain.com". And give them that address.
Or simply give them screen shots actually even easier and say it's pw protected and only open to selected users.
There is stuff to know, not a big deal, but hard to summarize in a HN reply.
We got a trademark by putting up a site which literally was created by putting a logo on a customink.com shirt, screen grabbing, submit that to the trademark office and say that was the product. This is not a patent. It's a trademark for a logo or for words, right? All you have to do is show you are using it. In general.
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.
