@MOAK Hearing people's experiences and thoughts on these things is always interesting. I find that most people generally prefer less structure and more action, but less structure with a group generally leads to more discussion and less action.
Opinions: I hate camping and dislike spending time at camp. I have done it right and I have done it wrong, and I hate both. I'm not opposed to stopping, but I am opposed to stopping where everybody else is stopping (such as parking lots) because they tend to be uninteresting to me. That being said, I only travel to get to places where I can go off-roading, so I'd rather stop in a boring place if there is more than one vehicle in the group, because otherwise, we will be stopping when we get to the first obstacle and the first guy breaks a tie rod or a drive shaft or some other thing he should have inspected before. I prefer being tail gunner in group runs because (1) I don't have to pick where we go and what we do and (2) it's fun picking up the pieces that fell off everybody else's rigs, and/or pulling people back out of all kinds of glorious stuck conditions. Always bring a walkie-talkie, even if nobody else does. Alcohol and off-roading were a combination devised by Lucifer himself. I hate mud. Never stop on sand. If there is a road, there is a road for a reason, and at least one wheel should stay on the road at all times, particularly when stopped. Go as slowly as you need to, and as fast as you have to. Momentum is everything. Stance as wide as possible and as tall as necessary. Learn to drive backward as well as you can drive forward, because you can't always turn around. If you can't see in the dark, don't drive in the dark. Only stupid people think danger is fun. Bring snacks, and eat wherever you stop. Bring all of your recovery gear, every time. If you don't bring it, that's when you will need it. Running with a group offers trade-offs as opposed to going solo.
With that said...
You & Honey Pros:
You can go wherever you like, and stop wherever you like, for as long as you like, provided that you both agree on what you're doing. You also get to have the wackiest of conversations which will be forgotten as soon as you get out of the car. A second set of eyes comes in handy, provided that it is focused on the path ahead and not on the telephone.
Going to take a detour through a town you've heard of, but never seen? Want to hit the mud pit today? Stop and go out on the board walk or look over a cliff? Spend an afternoon at the library? Whatever makes you happy, there's no group pushing you along.
You & Honey Cons:
If you and Honey don't have the same idea of fun, and/or if the two of you don't agree to do things you don't feel like doing at the moment, you're not going to get much out of the trip. Bad attitudes, impatience, and lack of communication (dudes, figure out whether she really wanted to come with you, or if she'd just doing it to make you happy because you fixed the bathroom floor last July) can make a You & Honey trip really bad, really fast.
You want to go out for a picnic beside a remote lake in the mountains, but she wants to pull out the dirt bikes, somebody has got to give. You can still have a good time either way, but there will be compromises.
Solo Pros:
Absolute freedom. Just you and your gear, limited only by your knowledge, judgment, and skills. Respecting the law is nice, too.
You can stop anywhere you like, take any detours you like, and invest an afternoon in poking around a particular spot you liked because it had good scenery/flora/fauna/food/a car show was happening there, or whatever else interests you.
Solo Cons:
When your poor judgment and lack of skills gets you into a bad situation, there's nobody to help pick up the pieces.
Bad weather? Sick? Robbed? Stuck? Rolled over? Too bad!
Multi-Vehicle Pros:
More vehicles means more forgiving stuck conditions - your buddy gets stuck, you can pull him out quickly, and the other way around. Also, if one vehicle becomes incapacitated, the other can be used to get to safety until a recovery can be attempted.
Multi-Vehicle Cons:
More vehicles means more occupied space on any road or trail you use, which means that turning around can become a very complicated affair. This also means that the minor amount of trail damage you may cause on your own will be multiplied by the number of vehicles in the group, which can be very bad in some environments (not just bad from the EPA's point of view, but can render some routes impassable, meaning you can't come back out the way you went in).
Big Group Pros:
There's usually some kind of hierarchy, and a role assigned to each person. The food guy, the tool guy, the winch guy, the cheap-truck-and-big-mouth guy, the lead-foot guy... We all know the roles, and we all know which ones we prefer to be (and which we prefer not to be). Whatever you "might" need, somebody in the group probably has it.
Big Group Cons:
There tends to be larger amounts of time spent stopped and in discussion of what will be done next and where we will be stopping again. The sheer number of vehicles brought means that tackling any single objective will take much longer - even if each objective takes only a few minutes per vehicle, some thing that takes 10 minutes solo can take an hour with a group. No matter how quickly you can tear down and pack up, there's that one guy who can't figure out how to put away his tent, or doesn't know how to use ratchet straps, or has to stop and refill his gas tank every 20 miles (this one is me).
