Thanks for the GIF, that's definitely unexpected behavior so let's do some diagnostics.
It looks like the track is frozen. Normally if you have two clips in a track and then freeze, they will
appear to bounce together but the clips remain separate so that you can return to the unfrozen state. I rarely use freeze, but what happens if you unfreeze, and then either re-freeze or try to bounce the unfrozen clips?
Also, what happens if you bounce each clip to itself, and then try to bounce the two together?
As to the dynamics issue, I assume you're exporting to a stereo mixed WAV file. If you create a new SONAR project and import that WAV, a) does the waveform look correct, and b) does it sound correct? If not, what does it sound like if you open it in a Windows playback option, like GrooveMusic?
Finally...what kind of audio interface are you using? If you're using the computer's internal audio, Windows might have some default "enhancements" that are intended to create consistent levels in a playlist or alter EQ. I've been trapped by this multiple times when creating audio on my desktop machine, bringing it into someone's laptop for playback, and then having it sound horrifying.