Hoping you guys can help me on an issue regarding my ticket.

So my ultimate goal is to get to Prague. I found a roundtrip direct flight for $133 on orbitz.com from BRU to PRG, and coincidentally it's on Brussels Airlines. The connection times work out good enough... I land in BRU @ 8:50am and the BRU-PRG flight departs @ 3:55pm. And on the return, I am flying in a few days early to explore the area around Brussels.

I'd like to buy some sort of travel insurance for a couple of reasons. Mainly, I'd like to be refunded for the above inner ticket in case my LAX-BRU ticket gets canceled. But secondly, I'd like some sort of recourse if I miss my YUL-BRU flight somehow (I only have a 45 minute layover in YUL) and have to take a different BRU-PRG flight.

None of the online insurance companies seem to cover if they offer any benefits for multiple itineraries. Is this possible? And is there any magic I can pull with Air Canada or Brussels Airlines to somehow merge the two tickets into one itinerary once I've booked, at least solving the missed connection problem?

Appreciate the advice!