One thing I find interesting about WordPress is how easy it is to get a site running, but how quickly the complexity can increase once the business starts depending on it.

A basic brochure site might work perfectly well with a suitable theme and a few plugins. The challenges tend to appear when requirements become more specific.

For example:

• A plugin update breaks a customized workflow.
• Several plugins introduce overlapping functionality or unexpected conflicts.
• A client needs a feature that almost fits an existing plugin but requires extensive workarounds.
• Performance problems persist even after basic caching and image optimization.
• The site needs to integrate reliably with an external system.

At that point, adding another plugin isn't always the answer. Sometimes the right solution involves debugging the underlying issue, reviewing the architecture, writing custom code, or replacing an unsuitable component.

For a business owner, the difficult part is often recognizing when continued DIY troubleshooting is costing more than getting the right technical help.

Where do you draw the line between maintaining a WordPress site yourself and bringing in a developer?