Drupal doesn't have a steep learning curve, nothing more steep than any other CMS. It's just made by web developers for web developers, that's all. If you're a web developer you can relatively easily adopt to the Drupal family as you could to any other CMS. It always take a bit of time to understand how everything works, how they handle updates, functions, hooks and whatnot its just part of the game.
If the TS has worked with Drupal before and knows his way around, I'd say use that platform again. Sure, WordPress, Drupal or Joomla, they're all about the same based on features but where WordPress stands out from all others is it's accessibility over all others.
Your neighbor, your sisters son by the age of 12 - they can all use WordPress, install it and start creating websites, adding plugins do some fancy stuff that alters the website and go with the flow even if the have no development skills at all. I bet you in about 8 - 12 months those people have learned so much about creating websites by just adding features to their WordPress website that they start to like it or understand what real web development is about.
Now let's do the same with Drupal, your neighbor or that 12yo kid probably doesn't even get any further than downloading Drupal on their computer and now what?
As soon as you log into a Drupal or Joomla dashboard it can become very uncomfortable for someone without exciting knowhow about managing websites. Maybe the TS also has another bike member of his club who also like to contribute to the website, maybe handle the calendar stuff or write blog posts to attract new bikers, most of the time those clubs can use all the help they get.. What if this person really would love to help out BUT he has never seen a dashboard of any CMS before. It can become very overwhelming very fast if they log into a Drupal site for the first time. That's where WordPress stands out from all others. WordPress isn't just made by web developers for web developers who then create a website for client X so he/she can manage his website. WordPress is made by everybody. They have a few people on the core team that can't really write a single line of code but all they do is make sure those web developers who do code all the time don't create features that stink to use for non technical users of the software.
A simple example, just Google at: Drupal dashboard, Joomla dashboard and WordPress dashboard and look at the images that will pop-up in the results. You'll see in glance what I'm talking about. The WordPress dashboard always stays the same for everyone. If you're a user with a very advanced website of just a personal blogger you happen to have the same dashboard. This is done for a reason, because if John has a problem with his WordPress website, he can ask Cindy who happen to own a WordPress site too and she can guide John around based on her experience. She knowns the publish or help buttons always will be on the same position no mater how advanced John's website may be. That's also the power behind WordPress but you'll never notice those things because you take them for granted.
WordPress is way more 'social media friendly' -like created. If Facebook, Twitter and all others would happen to have a dashboard or back-end platform like Drupal has the regular people around the world probably couldn't use it because it isn't friendly to navigate around, they would give up on it because it would become a pain in the * to publish something fast if you're not an experienced user.
Back on topic, feature wise you could use whatever 'populair and mature' CMS you like, they all have those features.
If you would use WordPress I can recommend the following plugins to advanced your WordPress site..
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WordPress SEO ( if other bikers have to find your site )
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Easy Digital Downloads - Don't let the 'downloads' part in the name of this plugin fool you, this plugin does everything so well if you just like to sell stuff online, if you want to sell anything
without shipping physical products to customers this plugin is what you need. It's super simple, you create products and you add them on a page where you want them to show up..
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MailChimp ( vistors can subscribe themselves to your newsletters )
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Database Backup ( safety first )
There are so many great plugins, I know for a fact there are about 3 really book calendar plugins around but I don't have the experience to tell you which one is best so you better just Google: WordPress + calendar plugin and I bet you that you'll find a plugin that does what you want it to do.
Same goes for social media buttons and stuff like that. You can use the JetPack plugin created by WordPress itself that will do the trick for most users but there are so many advanced plugins in this field. It's too specific for what you probably need.
Long story short, it's all there... And this is not a WordPress selling pitch because you can do this with about every other CMS around not just WordPress. The only difference between WordPress and others is how easy you can find all this information online and use it. If you have a problem with your WordPress site, Google it: it it's likely you'll find a solution within the first 5 Google results because it's so populair that chances are someone just like you had the same problem and someone else gave a solution for that problem.
My advise start locally creating on your computer. Install
MAMP (Free version) on your Mac, this creates some sort of fake webhosting on your computer so that you can install and test WordPress or any other CMS on your computer without internet connection. It's great for testing new features on your site before you publishing them on your Live website and maybe ending up with a problem or two that you have to try and tackle after while very site user can see those problems.
There is even a helpful
WordPress documentation about how to do this.
Just go with the flow, install MAMP on your Mac + a CMS of choice, pick a theme ( web layout ) you like or a theme that looks already near 75% of the end-result how you would like your site to be in the end and just go with the flow. The 25% customization you'll do later together with the community. They will help you change colors and what not. Just never ask web developers to create a website for you. But ask them friendly how you can change the background or a button on a header item and they/we will help you. No problem.
