What's a reasonable price for this menu bar app?

Honestly, I'd go with a time limit on the trial instead of a free version. Why? Free users are great, but they may NEVER convert. If they have free access to all features, they are more likely to get "stuck" and then upgrade to continue their life uninterrupted.

I'd say 15-20$ is more in line with where I'd expect the price of this app to be. Hell, I paid 15$ for bartender (twice, since they made me pay to upgrade, if memory serves) and all it did was let me hide / reorder menu items (fairly unnoticeable once it was setup)

$5 sounds pretty cheap to me. This is a tool that will often be used in professional contexts so try not to think as a consumer.
If it is really user friendly, with good search and a possibility to sync between my workstations I would pay $20.
The syncing could be a compelling pro feature (maybe via a file on Dropbox or something so that you don't have to build a webservice yourself).

Looks like a very interesting product, and I would definitely use it. (signed up to your mailing list)

I'd pay about $10 for a menu bar tool.

Finding the right price for such a tool is really hard. I've been through the same chore recently for my Mac desktop application Tablecruncher. I've been looking for similar products and their pricing. Similar here doesn't mean they have to do the same. It means addressing the same type of users and offering similar time savings or productivity improvements. With my application I have some direct competitors and I'm using the price to differentiate my product from those products offering less functionality. Another indicator has been the price of the same kind of product for Windows.

That said, I'm inclined to say $5 is too cheap. On a gut level I'd think a price around $10 - $15 would be okay. But this depends a lot on the presentation of your tool. Try finding examples that help to save time. One example: I had to regularly restart the bluetooth daemon on my iMac, when my mouse disconnected. Your application would do this with just a single shortcut. Would have saved me a lot of trouble.

So, search for tips out there involving the command line and use those examples. Recently I came across a command to rebuild the launch service database that fills the "Open with ..." context menu. A lot of people seem to have troubles with a very slow context menu.

Oh, and one last idea. Use one or two GIF animations on your landing page showing your tool in action.

$5 already seems pretty cheap. Doesn't seem like you could go lower than that. If anything, maybe you need to raise your price. The cost of something shows its value. Your kind of telling your potential users that this isn't that great based on $5. You want to sell that this can save them a lot of time that is valuable.

Maybe you could drop the free tier and have a trial period instead so that you don't have to worry about the contrast in free to pro version.

I agree to what most of the others said. I feel that 5$ is too cheap. Other apps want more for less.

But here comes the point. Don't compare your pricing model to the ones that you compare with. The right question is: What value do I provide with my product. Based on that, think of a price. If others have more features but provide lesser value because the product is hard to use, then you should not compare with them.