I always argue in favor of something a little more interesting, such as a city in the interior of the country: Santiago, Moca, La Vega, San Francisco de Macoris, Mao, San Jose de las Matas, and Jarabacoa depending on how adventurous you are.
My reasoning is this: White sandy beaches are available in a lot of different places, so why just one? And ex-pats, the ones you want to be with, do not party every night, and they are, in fact kind of quiet folk. And finally, partying every night can be boring after a while.
And then you talk about mountains. The Central Mountains ARE interesting and present a lot to do. Down in the Southwest there are cloud forests, over in the East there are Rain Forests. For the hikers there are paths all over the place.
So consider locating yourself, say within a certain time/distance of beaches and certain time/distance to mountains, something you are comfortable with. For example, in the little town of Mao (west of Santiago) you are 1 hour from beaches, and1/2 to 3/4 of an hour from mountains (less if you go on a mountain bike) and the trips are interesting, too.
And to all of this, you are in a Dominican society, not a beach society where it seems to me that everyone is out to get your money. And the added plus is that your housing budget would be hugely reduced giving your more to spend on traveling and learning.
At least think about it, since the DR is a whole lot more than beaches...
Regarding your overstay, you can always apply for visa extensions, those are no big deal, and the overstay fines are very reasonable, and have no repercussions on your residence application.
I can understand how a person coming from a very well organized society where everything is considered to be transparent can get lost (psychologically speaking) in the whirlwind of Dominican living. Nothing is as it seems, and nothing seems to work as it should or as it does in Canada. So the Word is this: Patience. The outcome will be : Understanding of a new and different lifestyle.
And peaceful living and lots of enjoyment.
Cordially,
HB