Is it better/cheaper to buy an unlocked phone in Canada/US (which is where I am) and simply get a SIM card with a plan in the DR once I arrive or just get a local phone with the plan?
as a newcomer, it will not be so easy to get a plan (best chance is with orange)
get a samsung galaxy s 4g by tmobile (craigslist) and I will unlock it for you free. Then you can hook it up with orange or claro.
This phone is an android phone and will do much more than just making and receiving calls. Now if you just want a simple cheap phone, you can get one here for 10 dollars, activated by a card.
AZB
prepaid cards.
It also depends on where you are. In areas with lots of expats it will be easier to get a prepaid plan, if you pay a deposit of 1 or 2 months. Frequently they will ask you local references, or proof of a Dominican bank account (for which you also either need property or references)
Not looking for a phone I'll get stolen... something that can make calls, sms and perhaps get online with... but nothing extraordinary.