Two concerns: Available for security updates / Image captions I am looking at revamping a set of sites from ASP to Drupal. I like a lot of what I see in Drupal, but have two concerns:


In reading about Drupalgeddon, it seems that the problem was that many people didn't even see the security notice before hackers started exploiting the vulnerability. I have no staff, so this means I need to be available immediately to install security updates when they are announced. I don't know that I want to be chained to my websites that way, or leave them potentially vulnerable if I decide to go on vacation for a month.
I've been amazed to find that Drupal has no innate ability to put captions on images. Doing that appears to require choosing between three modules (Image Caption, Image Field Caption, or Image Caption Formatter) with no documentation that compares and contrasts the modules to help with the choice. Putting captions on images is a pretty basic requirement, so it makes me wonder what else I'm going to find out I can't do easily once I start porting content.


Comments?
No matter which CMS you use this will always be an issue. If you do not have time to be proactive about maintaining your software, you should look into paying someone to do it for you.
This is the result of Drupal's modular design. It's done this way so it can accommodate the wide-spectrum of use cases. It's a simplicity/flexible tradeoff that can be good and bad depending on the circumstances.