Housing has always been a challenge for me, too. It's expensive, but what I've found to work well is to set up enough of those cheap bunk-houses to accommodate 100% of my population, and then start building regular (no electricity) houses, so that people have something to earn. I then strategically place decent (again, no electricity) apartment buildings close to my main centers of commerce/industry. When enough people have moved where I want them to move, I start cutting back on the bunks.
I also intentionally do my best to ignore mining, unless it's gold. Leftover iron and bauxite mines are great to fall back on, if I really get into an economic crunch, and oil is well and good, at the end of the game, but pineapple, coffee, sugar, and other processible produce are where the sustainable money's at.
Mines also create a lot of pollution, and I like to avoid much of that, because tourism can be sustainable and profitable, too. If the tourist trade doesn't work out, I can always fall back on fine furniture (things to fall back on are good).
I try hard to feed my people well, too, with an eye on variety. That really seems to go a long distance towards increasing overall contentedness, if not happiness.
Crime is easy to put down--unrealistically so, really, it's never been a big problem. I almost wish it were, that I could better live out my Caribbean Voodoo Batman fantasies. Quite a lot of caves in the Caribbean... Education and literacy I find is very important, and I find big benefits in "home growing" atleast my highschoolers. The better to teach them the national language I've created for them.
Medicine is more of a challenge. Most, if not all, of my college-educated citizens, imported or otherwise, end up here, and I make sure all my most educated folk are payed very well, and have access to atleast newspapers. Citizens of 'San Presidente' are ofcourse taught that other languages are fine too, if you happen to like reading words that will give you cancer.
I tend to avoid too much electricity, atleast for most of the game. It's a hassle, and I don't always even need it, unless I decide I want hospitals. The palace is solar-powered, in addition to several large underground generators. The people are aware of this, and it helps tie into the whole Cult of the Sun President/Cult of the Bat Loa I've got going. Religion is a good thing. I also don't bother with an enormous military. All firearms are confiscated at the docks, and end up in my private arsenal, so why should I pay good money teaching my citizens that guns exist, or the particulars involved in employing the soul-poison my bodyguards' crossbows are tipped with? (everybody calls it soul-poison, but it's really just botulism) Apparently, the rebel camps don't come with smorgasbord, either, since the few rebels I produce always seem to get hungry and go back home. Fat and happy are my peasantry.
My personal bodyguard, however, are always the best paid folk in the Carribean. If I could, I'd make diamond pinky-rings and gold-plated remote-control brain grenades a standard part of their Armani uniforms. Keeping me alive and in power is what's putting their kids through the luxurious secret underground college-prison I built for them, and may someday even let them out of.