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!

In the short term I think you will get going quicker with Wordpress with some plugins that should enable what you are looking for.

But to make this decision I would first consider if this version of the product you are looking to build is just to test if your business can work - like an MVP (Minimum Viable Product) - or is it the long term version of something already tested and proven.

If you are still trying to figure out if what you want to do has any legs, then I would go with wordpress. Get it running in a few days and test everything you need to make it work. For example getting users, creating the content you need and learning how to convert visitor to paying members. If you spend a few week/months on this and you get answers to all the non-technical questions, you can also re-asses if it is time to build a fully custom solution.

If all the other parts are already figures out and you want a custom build technical solution that allows greater flexibility I would use Rails. Or some of the other frameworks like node.js or CakePHP.

There are also some software services online build for this. So make sure you look at them as well.

Ruby on Rails has some limited options for membership sites so it's likely you'll need custom development to get the solution you want. It's more likely that you'll find a WordPress plugin that covers your needs - including something like Paid Memberships Pro that is free but is super developer friendly.

Caveat: I advise on & build WordPress membership sites so I admit that I may be a little biased :)

You won't be able to build Clarity on Word Press. It's a content management system so while powerful is extremely limited compared to what you could do with Ruby or any other software language. But as someone else identified here you're comparing apples to oranges. Word press will give you a website quickly and you can make some tweaks and changes within the limitations of WordPress and it's plugins. Ruby on rails is entirely different - you can build whatever you want. Although it will take longer and cost more, you'll be able to create a web application as opposed to just a website. Hope that helps!

Full Disclosure: I'm the founder of ChimiChurri (see http://chimi.co). We build the kind of membership website/application you are looking to build by leveraging a proprietary product building platform and a professional services team. I'll attempt to keep my answer as honest / unbiased as possible.

The quick answer is you can likely build your membership website with either. But, WP is, IMHO, the wrong tool for the job. I have built WP sites and coded WP plugins before and, from a software engineering perspective, you'll likely very quickly end up in what I'd typically describe as "plugin mess". Meaning you'd probably end up with a duct-taped ball of WP + custom theme + several (different) third-party plugins + custom code + third party services that will be extremely hard to maintain and continue to iterate and build upon. So, while doable, you'll sacrifice quality and accumulate "technical debt", to say the least.

As per Ruby on Rails, it is a very solid MVC framework I have used to build many products and applications throughout my career, including marketplace and market-network type applications like the one you are describing. But, with RoR alone you'd indeed have to build lots of custom functionality to get to MVP or v1, and that will take money and/or time.

With Chimi (our product building platform), you can get the best of all worlds: a solid, robust Ruby on Rails application that has lots of the features you are looking for available out-of-the-box, without sacrificing quality, flexibility, or ownership, and with a relatively small budget and fast execution and implementation time.

With Churri (our professional services) you also get access to top-quality engineers and developers that can build custom features and integrations unique to your needs.

Let me know if you'd like to setup a time to chat - I'd love to give you a demo and see if we'd be a good fit for your needs.

Disclosure: I co-own the business that does both custom development and Wordpress development.

While there are number of plug-ins to organise membership website for Wordpress, I don't think that you can build something like Clarity there.
Like others wrote in your case Wordpress can be a way to test the water, prove that there is a demand for your solution. You'll get something running fast albeit you have to go with what is available rather than develop it the way you see it.
Sooner rather than later you will overgrow the platform: the solution will be too complex, to slow, to hard to maintain and modify. This is a point to leave Wordpress and develop custom solution with Ruby or other technology.

Should you start from Wordpress or Ruby depends on many things, the most important in my opinion are;
- Where is your innovation? Is it on tech side or more on business side?
- Can available Wordpress plugins meet at least critical requirements to your MVP ?

Feel free to contact me for further discussion of your projects.

Go for PHP

Rails hosting is going to cost you way more and you must take into consideration maintenance, e-commerce app development, widgets, etc. If you are on a budget and you want the better price, then I would go with WordPress.
You can read more here: https://www.devdude.com/ruby-on-rails-vs-wordpress/
Besides if you do have any questions give me a call: https://clarity.fm/joy-brotonath