Not Traveling Alone

As you can tell from my Sultan commentary, I don't like traveling alone, and won't do it again for a while. I have three trips in the works, and Bill will be there for all of them - Florida, White Mountains of New Hampshire, and a Cruise to Puerto Rico and some other places. But Florida and New Hampshire, well, they involve more than Bill and myself.
Tomorrow bright and early we are heading for Delray Beach, Florida with my mom - 83 years old, nowhere near death, but slow and fragile. We're house hunting in Delray for several days, in the worst heat of the summer, with a woman who can barely see, hears next to nothing. She's diabetic, has poor balance, and is no longer able to conduct a lengthy conversation or follow the logical progression of an argument for very long. She's emotional, defensive, sometimes hostile (and I'm not that nice, either). Since the house we're hunting is for her, we can't actually leave her behind, but I worry that she won't really be able to shop. Now if I didn't have other obligations, and I had all the time and money it takes, I could spend as much time as needed, see a few places each day, help her make a careful decision. But in the space of 5 days (including travel days), we need to see lots of places. We arrive Thursday afternoon and plan to drive around the neighborhoods we're interested in. Friday and Saturday must be concentrated shopping days. Sunday is reserved for second looks, and we come home on Monday afternoon. If we don't see anything good on Friday or Saturday, we'll drive up to visit an elderly aunt in Melbourne. I expect my mother will not hold up well, that I'll be too hot and too short tempered. Bill, of course, will keep either of us from really exploding, but I am truly worried about how to get along sharing one hotel room (Mom and Bill are both very interested in saving a few dollars) for what might be a very, very, very long weekend.
In August, we take Bill's 13-year-old daughter to an inn in Madison, NH (near North Conway). Could this be the opposite of my Florida trip? I remember the days when I took my kids to the country. At that age they truly resisted any involvement on my part in their activities, and I think it will be that way with Caitlin on this trip. So instead of my mom's neediness, whining, and demands, I expect that Caitlin will be whiny and demanding, but that once she gets what she wants, she'll want US to take a hike. I haven't taken a kid on vacation in at least ten years. Mercifully, she is the sort who occupies herself, and if she feels shy, she doesn't show it very much. Where I worry about the trip with Mom, Bill worries about the trip with his daughter - it wasn't his idea, it's for a whole week, he doesn't always like being responsible for her, blah, blah (it's blah, blah when the worry is his, not so with my worries...).
It will be very interesting (at least to me) to see how each of these trips plays out. I'll let you know soon enough.