Interesting post OP. I've met a couple where the hubby is completely cool with his wife escorting and swinging with many guys. I've seen her three times; once on a GB punt that hubby was at, and twice more as a swinger ie. No payment, with just me and her.
I got into punting because of lack of action at home, but I'm trying to encourage the wife to get into swinging and the way I feel at the moment, I honestly don't think it would bother me if she saw other guys. As for escorting, I'm not sure how I'd feel, but I guess if I'm happy with other guys fucking her, then why shouldn't she make a few quid out of it? A forlorn hope I feel but I guess it's all well and good talking about it, but until you're there, you'll never really know.