No, he wouldn't be alone. He would have been told that it's suicide to go out in the Grass alone, and besides, since he's part of a convoy, he'd have a bunch of other hunters with him, getting a few stags or whatever for dinner. So that would be a nice plus for me: RP with you AND get some Hunting/Tracking stats.
However, the other option is also interesting. You could brush up on your Stealth one night, but Konrad isn't quite awake and he catches you. Once he finds out how much Kelvics are worth at market, he'd definitely keep a close eye on you.
And as far as this season goes, he'll be in the Sea of Grass from the 80th onward.