What is rails?

You are comparing apples to oranges. WordPress is a platform, Ruby is a web framework. If you are looking to develop a completely custom platform, you could certainly do it in Rails, but you could also write it in PHP (like WordPress). I'd do some digging and see what is out there for pre-made software first before you build something from scratch. I'd imagine there are already plugins that would do this sort of thing for Expression Engine, Joomla or WordPress. No need to re-invent the wheel!

This list of gadgets that many full stack Ruby developers find useful in their work: 1) A mechanical keyboard offers a satisfying typing experience and can reduce strain during long coding sessions 2)Noise-canceling headphones or high-quality earphones help developers focus and block out distractions in noisy environments 3)An ergonomic mouse or trackball can provide comfort and prevent repetitive strain injuries 4)A portable hard drive or SSD is useful for backups, storing project files, and transferring data between different machines. Remember, the gadgets you find most useful may depend on your personal preferences and work style.

At this stage there are lots of decent web tutorials but I find Ryan Bates Railscasts some of the best for learning the technology. However if you want to just become better at Ruby and Javascript there is no substitute for good books. I've just been reading Avdi Grimm's Confident Ruby and I think it's an amazing book for showcasing good use of Ruby and patterns of Ruby code and API design. I wish I had suggestions for Javascript that were equally good, but I honestly have not read much in the Javascript space. I'd also suggest listening to some podcasts like Ruby Rogues and Javascript Jabber where they often review books and concepts that you can then go read. The Ruby Rogues mailing list is also a good place to discuss Ruby issues. For tutoring I can just suggest joining a solid experienced team as a junior developer and learning from them.

Depending on how many simultaneous users you want the application to be able to serve at any given time (peak), and how much processing your application does when uploading and downloading files (as well as other typically used operations), your hosting specification requirements may vary. But, to offer some basic guidance, you could probably get started with about 3 Virtual Machines (2 for load balancing serving the web application itself, and one running the database). I'd get them with around 4GB ram and 2 CPU cores each. These run at around $40/month each on Digital Ocean. You could also use AWS, SoftLayer, Heroku, and others, each with their own pros and cons. For example, if you use AWS you could (depending on which database you're using) leverage RDS for your database which could simplify your scaling and operations. I'd suggest you store the uploaded files on S3, Object Storage, or similar service (as opposite to serving it from the file system which makes it harder to scale). Hope this helps as a quick guidance. As you can see there's lots of options and details to consider. If you'd like to setup a call, I can certainly help you dig deeper into the different options and which ones would work best for your specific needs.

If you're looking for Ruby folks, go where they go - local meetups. Second would be online but you will need to mine Stackoverflow, Github and similar sites and realize that they get approached regularly so start engaging early (at least 3 months before projected start date.)