skipaway

Any travel insurance savants here? I am thinking of purchasing, but I clearly don't fit the niches carved out by the companies I perused on "insuremytrip". I'm going to finish up the back half of a oneworld RTW I originally purchased over a year ago. I'm planning on taking my granddaughter, although she will be on different flights. So I will be purchasing her fare (unless my award guy comes through) as well as reserving and prepaying some hotels, rental cars, tours etc. I usually go bare, but this trip has already been postponed once due to my elderly mother's fall and hip fracture. (with minimal financial loss). But this round I'm going to prepay probably $6-8K.

Specifically:
* I have to pick up my trip at JFK and have purchased a separate ticket to get there. Would a flight delay causing a missed connection be covered?. This provision in the policies seems aimed at cruisers on a single seamless ticket--one thing to get to the next cruise stop, quite another to get to Katmandu.
*If something were to happen to my mother or another immediate family member and I cancel, will I be reimbursed at all? I'm assuming I'll lose the value of my ticket since not paid within 15 days of purchase, but what about the portion newly paid?

I deal with insurance companies more or less obliquely, and it's been my experience that their knee jerk reaction is denial. (Except, bless 'em, USAA). Am I right in the perception these policies are developed for people making a payment to a travel professional? Are there too many potential loopholes in this cobbled together trip?