I wouldn't be paying him to do everyday things he should be doing regardless of where he lived.
If his bed isn't made, clothes not in the washing basket, towels not hung up, then he doesn't leave the house until they are. No money involved, simply being a part of a household. No lifts anywhere, because he isn't going until his things are tidy and his chores done.
Pocket money in my home was a privilege, not a right, and not payment for participating in my own life - ie making my bed.
If it were me, it would be a sit down serious discussion about expectations and being old enough to do chores, exactly what he is expected to do without prompting, and being a part of a family/household. Until he can manage that, then how do you trust him to carry himself in a decent manner when out of your supervision? If that requires your DH standing there when he gets out of the shower and telling him to hang up the bathmat for a week so he gets the picture, then that is what it takes.
My 5 year old makes her own bed, puts her own clothes in the washing basket, puts them away when they are clean and gets herself dressed everyday, it is part of living her life and it is what is expected of her, I don't pay her to do it. I think that sends the wrong message. That one only need do these things if there is an immediate and physical reward for doing them and that is just not the case in my house. FWIW, I know she is not a teen, but she does get pocket money and she does do her chores, and neither is dependent on the other, and they are never used to encourage or prompt for the other, itms.
Anwyay, good luck, I hope you can work something out before bub comes!
$60 per week?! That seems an awful lot. What does he have to buy with this money? Does he buy his own clothes, pay his entertainment and canteen lunches etc? My niece is 14, she gets $12.50 per week!
My 12 year old gas the capacity to earn $40 a fortnight, for 6 hours work a fortnight. This is above normal part of house hold, her room being clean, bed made and towell hung up is normal house hold stuff.
To earn her money she has to do an hour on monday and Tuesday and 2 on the Saturday she is at home with us. In that time she is responsible for washing her and her siblings clothes, including hanging out, folding and putting away. Main bathroom and toilet cleaning, washing the towels from main bathroom and changing bedding ones a month, I do the other bed changes during the month.
She loses money from what she earns for leaving wet towels in her room. So if she does everything and also leaves towels in her room she won't get the full amount.
In terms of behaviour if she mucho up she loses privileges eg, iPod, tv watching, electronics etc.
What LS said. He's part of the household, he pulls his weight or he can live elsewhere. Why should he? Because it's part of being a civilised human being. It's not fair? BS. It's totally fair. It's not fair that people should run around after him when he's perfectly able to use his hands, feet, head. He's 14. In many communities, he'd be out earning a living by now.
tell him to stop being a bloody princess and act his age.
Thanks everyone, ths is exactly what I was thinking. I'm going to show it to DH and tell him we are sending the wrong message. Paying him for stuff that is part of living in a household is not on.
We are going to have to sit down & rethink everything. Thank you so much for your input
We tried a similar system with our DD (although lesser amounts) around a similar age. The problem was, the reward/consequence was too abstract. The money is completely imaginary until they get it, and the time between when they leave the towel on the floor and feel the sting of the missing $$ is too long to really make the connection. We found that even when she got not pocket money at all, it didn't really make any change.
So we've separated chores and pocket money. She gets pocket money now but it is not tied to doing chores, and she's expected to supply her own toiletries etc, as well as funding her own (limited) social life. So she's learning about how to make her money last for what she needs. Re the chores, we thought up some more immediate consequences. Removal of devices is one that works very well here. They can be confiscated at short notice, and if the behaviour does not improve, further devices are removed. She's got down to none and having to do her homework in the library at lunchtime (without her laptop) and I can tell you there was a very sudden and steep improvement in her chore-doing around that time!!
Another thing that works (and I have done this) is to make them "practice" the chore (like, on a Saturday morning). For example, you could send him into the bathroom to practice hanging up the towels for 5 minutes. As if they clearly have some difficulty with it so they need to practice in their spare time until it gets easier . Ok so I wouldn't overuse this one but it does make a point. Alternatively, you could have him write down a list of all the chores you do in a day on one side of a piece of paper, to compare with his own (very short) list.
FWIW I think $60 is far too much pocket money for someone who already has an over-inflated sense of entitlement. Pocket money is something you get when you demonstrate that you are a responsible person IMO, it's not an automatic right. I would be cutting that right back (bearing in mind what his actual need-based expenses are), with a view to reviewing amounts when the general level of helpfulness/responsibility improves.
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. Ok so I wouldn't overuse this one but it does make a point. Alternatively, you could have him write down a list of all the chores you do in a day on one side of a piece of paper, to compare with his own (very short) list. 
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