I think it is fairly unusual for teens to want to do family stuff in the way they did when they were little. If you go out, give him the choice to come or stay behind. There is no way my youngest would agree to spend her 13th birthday with her grandmother and a younger child. This would be asking for rudeness and stroppiness on my part
. She'll be 13 in a couple of weeks and is planning to disappear with friends or if she can, the boyfriend, for the day. You maybe need to adjust your expectations. 
Is his money dependent on behaviour? Our DDs (16 and nearly 13) get an allowance monthly. If they deliberately broke anything in the house, part of that would be taken away for the replacement. That's a logical consequence - logical consequences for behaviour are important at this age when not much makes sense in their teenage brains. Try to make any punishments directly relate to the crime.
I also pay extra for chores done willingly etc. We have dogs and DD2 rarely wants to come out with us. If she stays at home I pay her £1 an hour to dogsit (much cheaper than a real dogsitter and can add up to £20 or so extra over the week for zero effort on her part). I tell relatives and friends she is dogsitting rather than she doesn't want to come - so she feels I'm a bit on her side. the feeling I'm on her side rather than someone making her do boring family stuff makes her more likely to be cooperative in other things.
Try not to row over things which don't matter. It's rare I see either DD before midday at the moment and my 16 year old is often up until the early hours. Who cares? It's her summer holiday. Likewise, you can rarely see the floor in my DD2's bedroom. It's her room, I leave her to it.
I try to say yes to requests if I possibly can. That way, they know my "no"s are for a good reason. It's not been easy, particularly with my youngest, who does stroppy particularly well, has had a boyfriend for almost a year now, and has some friends I wouldn't personally choose for her. But you will get through it. Just take it a bit at a time. And it's not failed family life; try not to look at it that way. Family life changes for all of us when our children hit teens. Teens can be very funny - try to find the good bits and don't expect it to be how it was 5 years ago. :)