Hi, me again

So I'm still pretty much a n00b at this travelling thing (this past june, before I discovered Flyertalk, I still thought that if you miss a connection for whatever reason, you were SOL and you had to pay for a new ticket, and I would always book overnight stopovers or 12+ hours connections ''just to be sure''...that's how big a noob I am) and I'm finally getting how the airlines work and all that. But in my defense, I distinctively remember 2 trips of my younger years, one to MCO where the flight home was delayed by 18 hours and one to POP that was delayed 40 hours and AC and TS gave us no hotels, no food, no voucher, no nothing but the right to sleep on the airport floor for all that time :/

So, on my upcoming trip to vegas, I'm flying LGA-YUL-LAS-YUL-LGA (which, of course is ~220$ cheaper than YUL-LAS non stop return ), and since I can only get my yearly 2 weeks of vacation on what we call ''Construction vacation'' around here (last 2 weeks of july, when half the province is on vacation) and so , of course yet again, AC just jumps on the occasion and triples airfares to anywhere out of YUL...

Now, I'm looking at fares to random destinations for these dates and LGA-YUL-Anywhere-interesting is 500 to 1400$ cheaper than YUL-Anywhere-interesting.

My problem is that I probably won't make any status and would probably be the very last one to be rebooked on later flights, since I just started travelling this year, so I'm worried that something horrible happens and that the first flight is 10 hours late and it just snowballs out of control and I end up missing 5 of my vacations.

Is that the necessary risk of scamming AC out of 500$? Does it simply come down to how much that 500$ is worth to me?