The insurance, if you can get, would be crazy and its only a matter of time of when a storm is going to take that house out in the next 10 years. 

Is that going to work?

Some of the features I am looking for (most likely there is not 1 single vendor who has all this built-in, but more of a technology stack that integrates nicely)Would something like propstream, carrot, and kixie be powerful enough to get rolling out the gates and still be efficient in your eyes?

Is that fair? 

I'd recommend getting multiple quotes from service providers to see what pricing is going to look like per square footage.Without too much information provided and depending on the size of your home it could be anywhere from $5,000-$15,000+

My father is pretty close to retiring and has had a very successful last couple of years of his career.

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

I don't mean to cause offense - this is me just asking a genuine question.

Haven’t discussed pricing yet but probably won’t get as great of a deal on this one but it is a beautiful log cabin with big windows and fireplace overlooking the water.

This is one of the treason to do a trust.