Not sure?? I think he is concerned like we are that this has moved so quickly. And concerned about Bob’s track record. He has not met Bob
I did ask ds if I saw red flags or had concerns with someone whom he was considering marrying (he’s not dating anyone, so this was a hypothetical question/preemptive strike) whether he’d want me to point them out to him or keep my mouth shut. He said I should point them out, but that he’d probably be defensive. 
Kind of a rock and a hard place issue for me.
That was perceptive of you to ask that question, and your ds sounds self aware and thoughtful (“he said I should point them out, but that he’d probably be defensive.”); that’s great—and you asking him that now, with this context of his grandmother’s situation, primes both of you to give or receive that information more openly if you ever feel it’s needed in the future.
I have parents and in-laws in CCRC’s. Men are in demand at that age group so the fact that he is going “outside” the CCRC is odd. There are many women his age there!
From a financial perspective, I would ask your DH to do a more thorough look at the CCRC. Sounds like they are established, but if you buy in and they go bankrupt…
There is nothing wrong with encouraging her to slow down, even if only for appearances!
As I mentioned earlier, I don’t think you have to give your opinions to MIL. Instead, simply ask her thoughts about why she wants to marry so quickly or why she might be hesitant to wait a bit longer and spend more time at the CCRC and with Bob, etc. You don’t have to take a position. Same with the other topics as to the various scenarios financially if she moves, etc. Just ask what she thinks or if she has thought about this or that, etc. without saying your point of view. Just act interested in her thoughts, such as if she has weighed this or that. You would not be telling her what to do (nor should you anyway).
Actually these questions do take a position; they lead in one direction, i.e., why not wait.
Dh called mil today. Hoping to have a meeting with the CCRC this week. Let’s hope mil and Bob get something set up. Have to see what’s available. I’m not sure dh shouldn’t take the lead on calling and scheduling something, but I’m keeping my mouth shut.
I honestly think that I will be having fewer discussions with mil about any of this going forward now that dh is jumping in. I’m going to try to be more on the periphery. I’ll still be in the know, of course.
Mil told dh she and Bob wanted to take us out to dinner while she’s here this week. Maybe she’s feeling guilty about her statement and leaving her purse at home when we visited her town 
Well, I guess it is a matter of how it is all phrased.
I’m not sure it takes a position to ask: “I’m curious as to your reasons for marrying very soon? What are your thoughts about spending more time at the CRCC before getting married? Then listen, but not offer an opinion. Or things like, “what would you do if Bob were to get sick enough to need assisted living? Or if he were to die? How would that work?” I don’t see that as telling her what to do, but more asking her thoughts and reasoning, etc. It can be interspersed with comments like “I’m glad you have found happiness with Bob.”
IMHO a query without judgment would be, “So how are you deciding on a date? Marry him right now or after you’ve lived with him for a year?”
@Hoggirl I don’t know your relationship with your MIL. Maybe it would feel like asking her too much about her thoughts or various scenarios. I could see that. Maybe you could see if your husband feels comfortable asking her about her thinking on the various aspects.
@oldmom4896 yes, that is another good way with the emphasis on “How!” (like her rationale)
Bobgate update:
Dh is meeting with mil AND Bob at 2:30 today at the CCRC. Wish Bob werent going. My dh will not mince words. “What happens to Mom if she and Bob get divorced?”
Too short of notice for sil to get up here, but she can be dialed in and put on speaker phone.
Hope the meeting goes well.
Excellent! I don’t know whether there’s a way to say this to SIL diplomatically, but it would be great if she lets dh mostly handle it. It’ll get confusing if she chimes in a lot.
That’s valid. I think she will let him take the lead.
I’m not comfortable saying that to her.
I would let your husband and his sister deal with their own dynamics.
One thing they want to emphasize is caring that their mother has an affordable roof over her head should something happen to Bob.
They don’t want to sound like they are protecting her assets for themselves.
They might a,so need to know what happens if MIL needs more expensive care…how does this impact Bob.
I’m sure they will be fine.
OP, keep your expectations in check. The initial meeting (which is often with a member of the sales team, although they won’t have that title) does not contractually obligate the CCRC to anything. Just a lot of talking and spinning and “Wow, that’s a great question”.
The subsequent meeting– with someone on the finance team or the director of the place– where they resort to legalese– is where the hard questions get answered. So I think having SIL on the phone during the call is fine. The contract your MIL will have to sign has multiple disclaimers that anything that was verbally discussed with a member of the team is not contractually binding.
But a good first step.
Mil and Bob already had their first meeting. So, idk???
All those questions are on there
@Hoggirl , I hope with all our opinions and comments we are in our own way supporting you too - and not just having our own investment!
I hope you all just get some answers and clarification to the process.
Yes, try to get answers IN WRITING about what happens if one of them needs higher, more expensive levels of care or dies so that the CCRC can’t say, well, that was just sales talk and not be bound by it.
Also, you H can be very cursory about what assets MIL has—just that she has sufficient for buy-in and sufficient for monthly fees.