A lot has changed since my first WordPress blog.

Recently, I had the opportunity to decide on a new blogging service. Starting something from scratch without alot of prior dependencies is a rare opportunity. Although WordPress is taking over the interwebs as the gold standard, I’ve heard only good things about Octopress and Tumblr. There’s also Medium and Svbtle but these are invite-only and inflexible for organization blogs.

Once you pick a particular service it exposes you to huge switching costs. Here are my requirements with a heavy weighting on medium/long term objectives.

1) A Pleasure to Post

I want to focus on writing and not worry about mundane details. I don’t want to be gnashing my teeth on month nine. I want to write, post, and get back to work.

WordPress
Posting with their rich text editor never quite formats it the way I want it. The need to shift-enter or add a tiny ‘< br >’ is frustrating, not to mention the constant need to hop back and forth to preview the article. There’s an overwhelming and often unnecessary set of options for simple posting.

Tumblr
Posting is swift and simple out of the gate. Switch quickly to rich text, HTML, or Markdown. It’s like writing a quick email.

Octopress
A hacker’s wet dream. A huge learning curve for non-techies. For maximum mileage, it requires familiarity with command line (CLI), plugins, and general HTML5/CSS/Sass principles. And you’ll need to know Markdown. That said, say goodbye to malformed posts, constant adjustments with ‘< br >’, and switching between ‘HTML’ and ‘Visual’ tabs in the wp post editor to align content correctly.

Update: From @octopress: “CSS/Sass knowledge isn’t required for Octopress anymore than it is for Tumblr. Also posts can be HTML, Textile, Markdown, etc.” Very valid point.

Overall, Tumblr wins here. However, Octopress wins if you’re a hacker.

2. Zero Fuss with Image Uploading

I want a service that requires zero thought for managing and storing image files of different dimensions. Ideally, I can avoid another step to rename, normalize, resize, or manipulate images.

WordPress
It does a good job with easy Upload Files and easy image manipulation. You can use the file picker or drag & drop the file into the drop pane with a nice progress bar. Pretty painless.

Tumblr
Insanely easy to upload photos. If you want to add a string of multiple photos in one long post, it gets a bit more complicated. You’ll need to know HTML to really tweak the layout such as aligning the image or setting the image property to 100% width.

Octopress
You’ll need to do everything yourself. Literally. You’ll have to find your own plugins, organize your own image gallery/directory, and create your own layout/templates. Octopress is an outstanding blogging framework (this blog is on it!). But probably a non-option for people with a dislike for the shell terminal.

Tumblr wins here (by a slight margin).

3. Full Ownership and Local File Storage

Minimal external dependencies such as external databases and tech stack. I want to own 100% of my content and rights.

With Wordpress and Tumblr blog hosting services, you’ll always be under their respective Terms of Service. It’s extremely minor, but some people might have issues with it.

By submitting Content to Automattic for inclusion on your Website, you grant Automattic a world-wide, royalty-free, and non-exclusive license to reproduce, modify, adapt and publish the Content solely for the purpose of displaying, distributing and promoting your blog. If you delete Content, Automattic will use reasonable efforts to remove it from the Website, but you acknowledge that caching or references to the Content may not be made immediately unavailable.

In contrast, Octopress really excels here. Not only can you store and backup your files locally, but you can easily integrate with GitHub for version control. Never lose your data and it’s formated in simple markdown for maximium portability. More importantly, your content isn’t held by Terms of Service of WordPress or Tumblr (now or in the future).

Octopress wins here by a fair margin.

4. Visually Delightful

Out of the box, I want a blog that’s up-to-par visually without requiring a ton of customizations. Some people love to tweak the look & feel for endless hours. I just want something that looks nice and unique so I can focus on content.

WordPress
The default Twenty Eleven/Twelve themes look good. However, the really beautiful, differentiated themes are generally paid themes. Moreover, the paid themes have their own custom configurations and weird quirky bugs.

Finding the right theme is also challenging. There are tens of thousands of free/paid themes and less than 10% are what you want. You’ll spend hours trying to find a good theme running 10+ tabs on your browser running their heavy demos. And after you customize the crap out of your blog, people will still immediately recognize it as a WordPress blog >__<

Tumblr
Tumblr doesn’t offer a lot of themes out of the gate. But that doesn’t matter. Not only are the curated set of themes awesome, they each visually look very different. In general, Tumblr’s themes look way cooler and more modern than the typical WordPress theme.

Octopress
The creator of Octopress, Brandon Mathis, spent a lot of time ensuring the base theme was classy and beautiful. As a result, the classic out-of-the-box theme is the New Kubrick. Simple and elegant with a clear focus on content. However, if you don’t like this initial theme, it’s a long road to customization without a lot of prior HTML/CSS knowledge (such as custom overrides).

Tumblr wins here. I like their small set of curated themes.

5. Web Performance and Easy Custom Domain Setup

With the long term view in mind, I want site scalability with minimal downtime. I want to easily set up a custom domain and/or subdomain (eg. blog.example.com) with the service.

WordPress
If you’re using WordPress.com, you’re out of luck. You’ll need to host separately using a very ‘Year of 2002’ MAMP/LAMP (Apache/MySQL) stack. You’ll need to deal with w3 total cache, SEO plugins, broken and heavy social plugins. For the non-techie, there’s a relative lack of documentation on how to create a custom domain.

Tumblr
The tradeoff for Tumblr’s ease of use is stability. Since you’re not hosting your own blog, you’re at the mercy of their servers. Unless you’re a massive brand starting a corporate blog, the downtime will still be minimal for a new startup blog. For custom domains, the documentation is super simple.

Octopress
Octopress’ deployment is awesome with easy integration with Github pages, Heroku, and Rsync. This blog is hosted on Github so server uptime and response time are solid. Last but not least, baked weblogs are super fast!

Octopress for teh win.

Overall Winner: Tumblr (corporate) / Octopress (personal)

Dozens of factors play into finding the right blog service for the long haul.

For a corporate blog, I’d stick with Tumblr. Easy group admin controls. Non-programmers can use it easily. Customizable themes to can match the look & feel of the primary host site. Overall, it’s a snap and joy to use.

For a personal blog, Octopress is amazing. Fast and highly customizable. Extremely clean, simple, and readable. If you’re a hacker, there’s nothing better than posting code snippets with Octopress. No wonder it’s blowing up.