For the past two years, my BF and I have spent time in Playa Del Carmen Mexico for NYE and for about two weeks. This winter, we are planning on staying for about 3 - 4 weeks and want to bring our 2 year old Yorkie along with us

Playa Del Carmen is such a great place and we have visited there about 5 times in the past two years.
Hercules is amazing. He is 10 pounds, very energetic and a social-able dog. After reading about traveling to Mexico with a dog, it seems pretty easy and I want to ensure that this decision is right. He usually stays with a family member, but keeping him there for about a month seems a little bit over stretched. I am looking for some honest opinions and feedback for this decision.

We have already begun looking for a pet friendly condo (we have family who has a condo in a great complex, so they are helping as well).
I would like some details on flying with a pet, how to make the adjustment and what to expect.
Thank you!!