When I first signed onto this site, I got a lot of flak for being un-educated, un-prepared, and taking unnecessary risks. Some of those people who tsk'd me have moved on.
Unfortunately, it seems that same Sailnet Nanny-ism has been beaten into my brain, because I found myself "tsk'ing" you for setting out with physically challenged passengers, no able-bodied crew, on a questionable boat, at night. That was wrong of me.
I'm not going to cluck my tounge at you. You did it successfully, conditions were benign, you are familiar with the area (at night too), Seatow was close by.
I kind of feel like your friend put you in a compromising position though.
One by one, people showed up that you were expecting to be able-bodied, and it turns out that they really weren't. The boat's systems are questionable. Your friend is the owner, but he put you in the position of "skipper", which is the position of supreme responsibility.
Continue to help your friend, but insist that the boat be a little better prepared in the future, if he wants your assistance:
Engine in reliable working order.
Anchor ready to deploy.
Helm station equipped so that the owner can drive and SEE where he's going.
Navigation lights in working order.
VHF in working order? (or bring your own hand-held unit)
I singlehand my 30 footer most of the time, so you should be able to handle his boat little to no help, IF the systems are in good working order. I admit that an Allmand 31 is a couple thousand pounds heavier though, so you'll have to work harder than I do.
Anyway, good on ya for getting them out.
I, myself will be racing in the CRAB regatta this weekend: