When I looked at the flights the flight out was in the $200 range and the flight home was in the $400 range. But, plan A was to book the flight out with my sister and her family using the reward ticket and then wait and see what happened, hoping the flights would go down and/or I would be able to stay the extra days. I didn't have much of a plan B, just to try and book going home with it.
So I called Jetblue and they only had a ticket for much later in the day that the family was flying out. I went to plan B and they had one late afternoon flight coming home. I wasn't sure I wanted to fly back so late, so I called my sister first. I tried to get off the phone with her, but she kept talking. By the time I got on the phone with Jetblue again the last reward ticket was gone. There wasn't really anything else that fit with my plans either, and I called like 4 times too.
I waited a few days and came up with Plan C - I would switch my vacation week to the following week and fly out on Friday and come home one Tuesday with the family. I called Jetblue and I should have asked about the return flight first but I asked about Friday's flights instead. They had a seat on each of the later flights that day so I took the earlier of the two. Success!!!! I may try to go standby on an earlier one, I'll see how things are going when the time comes.
I tried to book the flight home with the family but it looks like Jetblue changed he time of their flight. Their confirmation email shows a different time then their website says. I asked my sister twice to check that and she ignored me, so I figured out a way to check their flight and it turns out their flight was changed. I booked the flight and now I don't have to worry about it anymore!