That's correct re the headsail on a furler but even so methinks that even with hanks the headsail is never tight up against the masthead. My previous boat did not have a furler and I remember the headsail still stopped short of the masthead. Maybe all that proves is that my headsail position was not correct. You would still need some gap between the masthead and the headboard simply because under certain conditions you would have the luff tension looser or tighter. Personally I woudln't be worrying unless the gap is significant. As , I think it was Sailingdog, has been suggested maybe you just need to lengthen the pennant a tad.