MAMP

Support is via forum only. Documentation can be very poor, particularly around product upgrades (one expects more from commercial packages). Due to their poor documentation, I lost several years of development databases when porting from an old to a new computer (they don't accurately document the location of the database files).

Other sloppiness: dialog options for domain resolution don't do what you expect them to; the main hosts file is modified every time you set up a dev web (didn't used to work that way) -- worse, when you make changes, old hosts entries are not purged.

Just really sloppy lately. I originally used MAMP some years back because it was a little more buttoned-down than the MAMP stacks available at the time, but at this point in time you would do better with one of the cross-platform open-source offerings, like XAMPP (just to name one I'm familiar with).