Wow, that's some crazy unfortunate timing - I'm sure your fiancée and kids were very sad to hear you wouldn't be able to join them as planned. Hopefully your back heals quickly and you don't have to put the visit off for too long!
So, for the questions:
1. A swing might work, but knowing Gwen she'd get too excited and overly-enthusiastic and make herself worse...
2. Girls at Love 4 won't turn, but anyone below that once you hit Act Three has a chance to. Some will fight for your enemies and others will simply "nope" outta town.
3. Always possible that one of the Boss Girls will turn out to be a short, ginger girl. There's 40-something districts in the first map alone, after all! :P
From the description, your fiancée sounds Scottish. I was actually born there, and most of my family still lives there. So maybe they know her ;)
I've had no rest, no breaks and no weekends for the last four weeks as I've worked on this next update but I'll be taking a week off at the end of the month to recover a little, haha.
Fingers crossed for your quick recovery and that you don't have to postpone your trip too long!