I have. It happens to me when I am laying down additional tracks for any song that I am in. It gets to the point where I can't use the software monitor for the instrument that I am in the process of recording.
It is very annoying to say the least..
When monitoring through software, there will always be latency of some amount. You can minimize this delay by adjusting the I/O Buffer Size parameter under Preferences > Audio Hardware. If it's set too low, you may experience crackling playback or dropped samples, so you may need to try a few settings before finding a blanace between low latency and high quality playback.
If you are using several CPU-intensive effects, you can "freeze" the track (basically, it performs a dynamic background render of the track and updates this render if you adjust parameters) by selecting the FX track panel view and clicking the "Pre-render Track" button which has a small lightning bolt on it. This button is also available in the mixer.