The obvious benefit is having company wherever you are and having assistance if needed. Being in a group is also a big security blanket for those who are a bit unsure of riding or travelling.
If you have a good group, it can be a great laugh too. If you're lucky enough to find a good dynamic, it can be such great fun.. I can see why many people do it.
The downsides are the everyday logistics. Everything takes six times longer and it can be like trying to herd cats.
Filling your tank can take half an hour as some people need to pee, one guy has lost a glove, someone want's to re-pack their luggage and one dude is hungry and will only eat Brand X sandwiches so go wandering looking for one. Then there is trying to get the gang moving in the morning with six different sleeping habits, breakfast requirements and packing speeds. If you wake up at 7am and are packed to go at 8am, it can be tiresome to be waiting around in your bike gear until 11am when the last guy is still looking for his toothbrush.
Personally, I prefer a group or 2-4. It doesn't feel like a convoy and you can still split off in two groups if required. Someone can also go solo with the other three still in a decent sizes group.
The trick is finding people on similar sizes bikes, with the same kind of sleeping arrangements, budgets etc. If you're riding a DRZ with knobblies and carry all your luggage in a small roll bag and live off $10 a day then you're unlikely to be compatible with someone with a over-loaded GS who needs a hotel every night..
If you're resolved to travelling in a group then I think the best solution is to agree on a meeting spot everyday where you can all meet up to pitch camp and share a  together. That way if people go off solo it's not a problem.
And EVERY bike/rider should have the gear and information necessary to go solo even if they never do.
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Did some trips.
Rode some bikes.
Fix them for a living.
Can't say anymore.
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