$4 sounds about right for that. If you evaluate the meal at the actual price (and not the price before happy hour discount) it is like a 29% tip.
Group tipping can lead to trouble though on occasion. Two people split a check and one ends up only giving half the others tip. It's one thing if you, individually, want to go above and beyond, but when everyone is doing the average and one goes way under, it can make for some uncomfortableness because the others feel that they are covering for the other guy or something.
Personality is up to your discretion. If everything is perfect, but the waitress lacked in personality, I'm fine with that. Sometimes you get a server that will sit and talk to you and that can take away from the meal with your friends.

The only issue I have here is that your boss will be paying you the bonus. The people eating at the restaurant aren't the boss of the waiter. Now if this thread was about restaurants not giving waiters a bonus then I think I would agree 100%
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