Drewfus,

For the last 3 yrs I've gone in with my father who is in his late 60s.  He is not in the best shape either, but he is smart, tough, and knows his limitations (sort of).  Don't discount the extra toll it will take on you as the mule of the team.  After my last trip, which was my father, my brother and I, I realized that putting too much pressure on myself to accomodate the other members of the team presented as much risk as overworking or expecting too much out of the old man.  If he can carry one pack over a portage you and your group should be fine pacing yourselves. 

One thing I would be careful of is making sure he doesn't get stuck in suck mud.  That happened to my father on day one last year coming out of the Mack creek when it was a little low.   It took an awful toll on him way too early in the trip.

If he loves the woods, and knows himself then you will be fine.

My last time was 2002 or 03 so maybe someone can offer an update. the road's great until you turn off the main road. After that it gets narrower as you go. At some points past Dinner Lake it's just an overgrown, two wheel path at some point. (Fun when you approach the crest of a hill.) I take my car but more ground clearance would certainly be helpful. After heavy rains I'll get out and check the depth of any washouts to pick the safest route.

As far as safety aspects go, the only vehicle damage I've witnessed was at the French lot when a tree fell on a friend's car - so don't park within reach of any trees that look evil if you can help it.  

I have probably used the Beaverhouse parking lot 15 times or so beginning with 1975.  I have never had a problem.  The road is actually quite good and most passenger cars and van will have no problem.  There certainly is no guarantee that your car won't be damaged, but there is no guarantee that your parked car won't be damaged in Ely, Chicago or Duluth.

Westwood

  You SHOULD of bought a Lotto Ticket for sure