Welcome fellow Canadian. I stayed in several areas before I settled on the Playa Dorada/Puerta Plata area. Samana is nice but to me it’s a bit remote, and a bit overpriced due to the European influences in the area. Where I stay during the winter I have easy access to the two major cities, more frequent flight options, and a multitude of towns and beaches (both remote and popular) to choose from. Come down, stay in different areas and then decide. Don’t get swept up in the place and buy real estate until your absolutely sure you want to go that route. Rent first, learn the language, soak up the culture, and then decide what the future hold for you in this diverse country. You have the option of paying for an extended visa when you arrive. I do it and I have friends who stay for two to six months and pay the extended visa fees when they first arrive at the airport. It’s not that expensive.