I have a project going on where I use ripple edit mode to edit hour of speeches. While ripple editing works fine most of the time, it causes oddities and even crashes. 
 
Setup:
* "Ripple Edit All" mode.
* Latest CbB.
* One track, no fx.
* No tempo changes.
 
Smart Tool to Erase mode => Paint region and it will be deleted.
 
Problems:
- If painting area with more than one clip or one clip plus empty space on a track then ripple edit may not delete the hole entirely but only some clip (rightmost?).
- After using ripple edit for a long time CbB may crash (two crashes immediately after performing ripple edit so far in 5 hours of work).
 
I'd like to get an exact recipe to reproduce ripple edit flaws. Can you help me with this? I'm sure Noel & team would be delighted to get exact steps to catch and repair ripple edit.
 

I'm doing a similar task with ripple edit. Editing narration from individual sessions that could be up to 2 hrs long. I have not had any crash issues while using ripple edit but it can mess things up if you're not careful. I constantly toggle RE on and off because if I do other tasks while it's active the results can get strange. 
I have not had any issues with selecting across clip boundaries or blank areas. Whatever bit of the timeline I select will be deleted.
Sorry I can't offer any more thoughts on your problem.

I found a way to reproduce the ripple edit crash. It's not Ripple Edit All but Ripple Edit Selection, though.
 

- Select Erase tool
- Select Ripple edit selection
- By holding the right mouse button down, select empty area in a track.
=> Crash.
 
I sent a bug report to Cakewalk.
 

Inconsistency:
* Enable Ripple Edit All
* Select Erase Tool
 
1. Erase clip + empty area => both are deleted
2. Erase empty area => it gets deleted
3. Erase empty area + clip => only clip gets deleted.
Reported to Cakewalk.