Platform support
Things are always easier with a bit of support.
Jekyll is the standard for GitHub, so this makes it a logical choice for many. With that said, your results should be possible to serve with any webserver. This is, after all, the main reason for these systems to exist. You will also drop the need for a database, simplifying your deployment even more.
All webpages your tools generate should only be HTML, CSS and some JavaScript. Thanks to this, any web-hosting company can take your files and display them. You can serve static websites on most big cloud providers, usually on a free plan. The famous ones Amazon, Google and GitHub Pages are examples.
On many hosting platforms, you have to pay higher fees for dynamic content, so mastering this technique to write a website can also save you money.
Most regular web-hosting companies provide one-click installation of WordPress and other advanced functions, but you can get a website up and running completely without it. Deploying your site becomes important when you decide to use the website and change it regularly. Jekyll has a gem: Ruby, this connects to any rack server including Amazon, Heroku and Slicehost.
Hugo has similar features. In both cases, you install the CLI for the service and add the target in the configuration file. With Pelican, you can push the pelican directory there and let Heroku take care of the deployment.
As you can see, choosing the correct generator includes checking which cloud provider you want to use. Picking the correct one will make the process painless and save you a significant amount of time.
If you’re a do-it-yourself hero, you can otherwise use ssh and in many cases rsync to transfer files. Once you have set that up you should never have problems again with deploying your code.