My pets are currently in the resort (for how much longer I can't remember) and I am about to leave for three weeks. If I sign up my pets for another 15 days, will it overlap the the current days they are in the resort (which would be helpful), or will it cancel out and just put them in for 15 days?
No, sadly you can't sign them up again as long as they are ion the resort. :( They'll only come out of the resort when the time is up.