I’ve been thinking about this a little bit more… We can also break this down prisoner dilemma style and tease out some conclusions…
I think the big question becomes: what do you mean by AGGRESSIVE and how much does that change the likelihood of your success?
I think it varies on the hole and brings into question what strengths you are playing to…
The 14th hole of my home course has a creek about 150 yards from the green and it’s about a 240 yard carry… if your father in law puts it safely infront of the creek and you have a reasonable shot from his tee shot, obviously it makes sense for you to hit aggressively and carry the creek, even if that distance is a reach for you… there isn’t much gain left to be had by moving the ball closer to the creek, but a ton to be had if you can carry it and have 120 yards in… I think this is a situation where it’s obvious to be aggressive.
The 13th hole is all downhill with some interesting ridges… if you can get past the 200 yard marker, you will get some decent roll and have 150 yards in… If your FIL hits it to the top of the hill, and you are deciding between aggressively trying to get it to 100 yards, or making sure you just carry the hill and have 150 in… I think it makes more sense to take the high percentage play and try to have 150 yards into the green… (though if your father in law can carry the hill, it would make sense for you to get aggressive and see how far down the hill you can get).
My overall thought is: Both of you playing your father in laws ball is going to be a net negative for the team… He’s a 5 handicap from that drive, and you are likely worse from that distance… From your typical drive, you will play to your 5-7 handicap and your father in law should play to a lower handicap, as he will have less club in than he’s used to.
Basically, I think the strategy that works best for you in a normal round will work best for you guys as a team, other than in places where your normal tee shot will put you close to where your FIL is… unless you can cut off a huge chunk of yardage by taking an aggressive line.
I think your biggest advantage is going to be having your father in law with 2-3 clubs less into every green… hopefully he will have plenty of looks at birdies and you guys will make a ton of 2 putt pars.