You don't seem to be quite in the right mindset, if you go that way and feel like you are being forced you will have a bad time even if you are actually having a great time.
What time are you planning to book? it make a major difference in what is available, crowds, and weather (rainy or dry season).
Most hassle free -> do a direct fllght from Calgary. This means most beach destination are available but not all of them are available year round. Pacific side will be shorter.
Avoid anything 3 star or under in Mexico. Even 4 star can be iffy at times compared to Canada / US, but check reviews. Brand names (i.e. Riu) may be a bit more consistent.
Also understand you are on a beach in open room settings in most areas, not uncommon to get an iguana in the room. And it will be humid.
You also want to decide how much the beach matters. Cancun / Playa del Carmen / Tulum are Caribbean side with white sand / softer and less waves. Puerto Vallarta, Mazatlan, Cabo, Ixtapa, Manzanillo are Pacific side and rougher waves, but can be beautiful.
I would suggest just pick a 4.5 or 5 star with great reviews with kid friendly pools and you will be fine.
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