Based on my limited experience, if they don't have an answer or don't want to answer, they don't reply.
I'm not sure I agree with that. But that's how they roll.
They don't seem to like to give info about how HBD works beyond what's in the help sections or previous Dev Chats. This question would fall into that category.
The answer is you use the How Conservative settings to make an initial ranking. They you look at the results and adjust.
Looking To Be Drafted In The First Round seems to mean they will ask for 1st round money, no matter where they are drafted. You can look at draft histories to get some idea what they'll ask for. Probably Won't Sign ask for a lot. You'll see some of those in the highest paid 1st round picks. They are usually not worth signing after the 2nd round (if that).
You'll see some 1st round picks that got a little more than the guys around them. Those are probably the Looking To Be Drafted In the 1st Round guys. I've never had a problem signing them for a reasonable amount as long as I drafted them in the 1st round.