Adding maps to your web applications is easy and powerful. Dive into Maps, Rails, GeoJSON and more.
There are some really useful gems that make rails a great environment to build geo-aware applications.
Rails ActiveStorage system is very nice. It standardises uploads, so going forward you will want to be able to write tests that take it into account.
Setting up hosting on a linux VPS with Ubuntu and apache is not too hard, as long as you stay on the path.
Middlemanapp.com is a Ruby based static site generator. It is incredibly flexible, allowing the designer to use any of the ruby based templating languages, HTML or Markdown to build a site & content. Easy to set up, work with, source control and deploy it uses all the shortcuts and tools in modern web development. It is really very nice.