My Wife and I have been to Cabo San Lucas about 8 times in the last 10 yrs. Just went in Nov with our 1yr old. As for food, it wouldn't be a trip to cabo san lucas without having breakfast at "The Office". It is on the water along the main playa (thats beach to the loacals) right as you come into town. You cant miss it! Your table is literally in the sand about 20 ft from the bay. The Chorizo and eggs is divine. Partnered with a Tres Generaciones margarita will make you forget you are usually on your way to work at such an early hour.

Also, if you have a condo or room with a kitchen and don't want to pay $10 for drinks at the resort or eat out the entire time, don't forget your Costco card. The costco has cheap liquor and all the fixins that our US stores have. We usually go and grab foodstuffs for our lunches and snacks (read margaritas) then do our dinners out. Really saves some $$. Just my $.02