I'm an experienced house painter I'm certified and I have been working for communications for two years.. It's true that I don't have my highschool education but I did upgrade in college.. I also am learning spanish..I have worked hard and I have a good job in canada but I'm honestly not scared of my lack of college degrees in all honesty ... I'm 23 I didn't want to experience life sitting in a classroom . I prefer to learn by experiencing life.
Believe it or not, this is something to rely upon!
While house painters are a dime a dozen (more like a million) in the DR, most working in that field are seldom "achievers" that stick to good service as promised. They tend to come from the poor sector and lack uniformity in their work. Most paint jobs see the never ending "Ma?ana" that never comes, as the "normal" practice.
If you polish your knowledge and apply new techniques on cement walls, the results could be a good advantage over looking for a job in the DR!!!
Having English as your native language is a big plus, so too the fact that most new apartments in the DR are currently making lots of use of the gypsum panels for inside finishing.
Consolidate into buying top notch equipment in Canada, pack it and send it by door to door shipping to the DR. Nothing gives you more edge above the rest than looking professional and being rightly equipped for the task at hand.
Buying and branding painting uniforms, caps, custom pails, etc... in Canada will work wonders for you in the DR. First thing is first! Come to the DR not as a tourist on vacation, but as if you were to make a move from your present home to another town within Canada. Ask many questions no matter how unimportant they might seem then, but that later could prove very critical.
Living with a minimum budget in the DR is doable, as long as you curtail to the very basics your current needs and comforts. Do you need 24/7 electricity in the DR? Not really! Unlike in Canada or the US, people buy their basic meals for the day fresh. That's to say one visits the local produce market to stack on perishables, which can be had for pennies on the dollar. Others visit the local big supermarket chains, where power is indeed run 24/7 to avoid huge loses in that segment of goods.
For TV during blackouts nothing much will be missed, other than your daily fix of Novelas. Most people that use the internet on a regular basis, own laptops and a battery backup for their modems.
Refrigerators stacked with the usual suspects in Canada, are not the norm in homes without a power generator at hand. Most homes keep cisterns or water tanks for the loss of power and water times.
Transportation is very cheap in the DR! The cheaper the less safe and outstandingly most efficient. Being "Motoconchos" (a motorcycle) the cheapest, unsafest and most economic of them all.
Renting a place in the DR is tricky, to say the least. If renting to a Dominican the rate is competitive to the local offerings. If renting to a foreigner, the rates double or triple in a jiffy. They figure that since a foreigner, they're able to pay better and still find it cheap.
When you are ready to rent, make use of the local expat community links in the area. Since they got lots of connections with locals already, many can provide the best bang for your buck.
Safety is a major concern in the DR as of late! This is not saying that crime is overriding the town, but it has begun to include foreign nationals more often than not. That means that the usual foreign spots, like Sosua, Cabarete, Las Terrenas, etc... Have become magnets to criminals looking for easy targets and sure to have some money or valuables on them.
With that in mind somebody looking to experience the culture and living of the Dominican Republic, as you stated, should be looking more away from the coastal paradises and more into the big cities.
Transportation? It's a must to live in the DR! Let alone carry out a business...
Cars and other vehicles are very expensive in the DR. You have two choices: Buy one in the DR, new or used. Buy one in Canada and later import it to the DR under the foreign citizen moving to the DR exoneration law.
Both options bring their own troubles. If you buy in the DR, you get what you paid for, literally! That's to say that a cheap car is not really a "good" deal, but more like buying a lemon that still got some left over juice in it.
On the other hand, car repairs are cheap in the DR and pretty much they can fix everything wrong with the car.
Importing a vehicle using the exoneration law, will give you the opportunity to bring a "good" vehicle to the DR but still cut your only option to do so for the rest of your life in the DR. You can only make use of that exoneration once! I find that most people that come to the DR and bring their cars when they moved have kicked themselves in the butt for doing so without giving themselves a time to soak-in the country.
As with everything in life, the best planned moves are the ones that meet success most of the time.
Like I said before if you can get a job/biz in the DR, you pretty much will live a comfortable life here.