Welcome Kenny B ;D ;D

I think your gut is giving you good advice ;) ;)
BETTER, a more "civilized" trip with someone you're not sure about, than to get in to deep and realize you have to take care of yourself and your paddling partner??
The 2 canoe's and 4 guy's is a good idea as well if 2 of you are somewhat experienced and can watch the "rookies" ;D ;D
Its also a confidence builder for your buddy, why get him in over his head and feeling like he's not carrying his weight, when a milder trip will sharpen his skills without putting a burden on you 8-) 8-)
More than one potential paddler has been turned off by being included in a trip that was way over there heads!!
People do it to there kids and there friends not realizing that for some, a "wilderness" trip can be a exciting but scary time especially if they have limited experience :-/ :-/
Maybe go just deep enough to wet his appetite but not so far you can't get out easily if the situation turns sour??