I'm not really sure how to work the Tropico 1 economy, especially if I'm evil. I've had plenty of successful capitalist tourism games, but even then I spend the first ~10 years or so mostly in negative money. Going by memory of guides, a lot of other people would be able to do things like profit enough to buy a church by year 3 whereas I'm just plain broke after year one for some time.

It's hard to google guides nowadays because they are all for Tropico 3-5, so I can't find the classic guide.

One thing I may not be doing right is roads. I don't prioritize them at all and really only start building them in year 20-30 when the economy is working (as a capitalist). How can I have a viable island where I'm an oppressive despot when I can't even afford to shoot dissidents?

Hi,
Just get 1 or 2 tobacco farms, and 1 or 2 mines.
You can just switch 1 corn farm to 1 tobacco farm at the start of the game. Then build 1 iron or gold mine.
That should you get enough money at the beginning of the game.

Also, make sure that there is housing near the dock so your dockworkers don't have to walk far to get to work. Sometimes I've had to evict people repeatedly from housing until the dockworker moves into the closer housing.

Make sure it is easy for your teamsters to move the goods to the dock quickly. If you can build roads for them to use, that's even better; but teamsters take the shortest path, which isn't necessarily along a road. If you want them to use roads, you'll have to see what path they are taking and build the road there.

I tend to keep a dock at full employment even if they are often idle just so I can always have someone there to load the goods as quickly as possible.

Speaking of loading goods quickly, build a road under your dock so the dockworkers move faster.

These four things should help keep goods flowing smoothly so that money keeps coming in.

Thanks for all the help, that makes the game start much easier. But I still can't ever get to anything resembling a positive economy. On my last island, I had a bauxite mine and gold mine going full force. I also had a jeweler shop. I was able to build all three in the '50s, which was great. In the early 70s, I was ready to build a power plant. Once I had that, it basically zero'd to -40K+ super quick. It ended up being a close tie between a US invasion or a coup. It was a coup. It's pretty much always a coup. Except when it is a civil war (which is always AWESOME). But I feel if the economy wasn't fucked I wouldn't have this problem?

Disappointingly playing Evil is so much harder than playing good (or at least capitalist). If you want to be a military dictator you might find it easier to play the first 10 years or so as 'good' to build up your economy and then switch to stay in power/