You know, bringing someone on a $2000 vacation IS awesome. That is a GREAT "benefit" for lack of a better word. But from the other side of the equation, I can also see where that could be pretty intimidating and you would have to ask just the right person. Sure, you are offering someone a VERY nice opportunity, but you are also asking them to share a room with you and take a week off work and away from their normal life. Now, before you say I didn't read your post and understand your options, I DID read and I DO understand the options you laid out and you clearly know all these women and have shared intimacy with at least part of them, but my point here is that while it is indeed an amazing offer, it might be overwhelming. Like #4, I don't get the sense that you have had an intimate relationship with her, despite knowing her for a number of years, so that might be kind of overwhelming for her to think about, particularly if she hasn't been divorced for very long.

Sorry none of the options you had hoped were viable didn't work out. Here's hoping you find a suitable option SOON or get more time to look.

Me 50, H52
Divorce from XH final 12/17/2014
Marriage #2 12/31/2019
5 adult (step)daughters (3 from XH's first marriage, 2 from current H's previous relationships)
4 grandkids (plus 2 on the way)