Hi Michelle! My husband and I just moved from the US to Las Terrenas last July.
1) We currently pay about $50 each for a very good health insurance plan with Humano.
2a) Real Estate attorney: Cesar Calderon with Guzman Ariza in Las Terrenas. He's helped us with 3 purchases as well as registering a US LLC here that manages our rental property.
2b) Immigration attorney: Lishali "Lily" Baez - 809-860-1231. If you read through the pinned threads on residency, you'll see quite a few of us here have been very pleased with her services!
3a) When you receive residency, you'll be able to bring in a 20 or 40-foot container of personal household items duty-free, as well as receive a discount on the import of a vehicle if you want to bring one in. We shipped in a 40' container with our car and the household items we decided to bring down here. We didn't bring a lot of furniture but did bring electronics, kitchenware, and countertop appliances. The selections here are not as extensive as you have at home, and the prices can be significantly higher since almost everything is imported.
3b) We brought our dog down in December after we obtained our residency and once we knew the temperatures would be low enough to allow transport in cargo. Our George is just over 20 pounds, so he couldn't go in the cabin. If yours are small enough to go in the cabin, it will make it much easier and the temps aren't an issue. There are health certificates required, but your USDA equivalent should be able to provide you with the details on what is needed. Be sure you fully understand your airlines' requirements as well! We know of people that have had to scramble at the last minute to get a crate that met the airline's requirements - size restrictions, metal fasteners, etc.
4) I can't offer that much here since I'm not Canadian! I think the biggest con is that we can't get Amazon orders delivered the next day (it takes about a week and we pay $5/pound for shipping from Miami). We have learned to make do and plan ahead - stocking up on items when we make trips back to the US. The pros are so numerous! For us, the fact that we were able to retire now is the biggest plus! If we stayed in the US, we'd be working until we could qualify for Medicare because the cost of health care is just way too high! The weather, the wonderful people, the abundance of fresh fruits and vegetables, the beautiful beaches...I could go on and on! It's been a bit challenging for us to make the move in the midst of the pandemic, but we've still really enjoyed our time here so far and have met some wonderful people!
Any help I can provide on Las Terrenas, please let me know!