I suspect Mr Big Cheese would quickly drop his moralizing.

When people get only texts or a form, it can seem suspect because that's how scammers operate.

Your time is valuable- if you need to hold for 5 years, as you suspect, well then you'd better be finely compensated for your time(and trust me, there's time involved) and for locking up your capital.

I do know that as your list grows, you might want to look at a campaign manager - regular email providers eventually think that large mailouts look like spam and they get blocked if they suspect thats the case.Campaign managers like Mailchimp and Constant Contact for example, allow larger mail-outs without that risk.

I suspect there's pros and cons?

I get 2 or 3 calls every week from "Suspected Spam." 

@Matt I.I suspect that if you are not getting bookings (airbnb or off platform) his other clients are not either.

I also suspect she waited to the 11th hour intentionally in hopes we would still use her with worse terms. 

If so, (I suspect that will be yes) you should add them as an Additional Named Insured on the the policy.You mention later that you have Umbrella policy.  

A few years later, decided to replace the cement walkway that surrounded the perimeter of the house, widening it, which  suspected was another source of the flooding, had the walkway angled out, so rain water would flow away from the house.