I can speak only from the WebOS side of things but my TP was giving me problems.
I.e. I couldn't transfer any files to the /media/internal no matter what I tried, regardless if it was using the wifi sharing app or plugging the usb.
I was getting the usb popup and when I go on and connect it - it tries to connect and then drops the usb connection.
I'm lucky to have a second TP with almost no patches(my wife's).
So the not so patched one does work fine thru usb so I figured it's not the driver or specific pc that couldn't connect but rather TP was to blame, since my pre 2 and the other TP worked just fine.
It looked like something was preventing mounting the /media/internal.
So I enabled back the logs on TP and removed LunaCE and UberKernal(which I toght might be the issue with CIFS shares since I messed with TouchPlayer and setting windows share to be available).
Anyway enabling the logs and turning on luberjack revealed that for the TP (because of issues with that VOIP client not working on the TP but fine on the phones) somebody came up with a hack to re spawn the service that connects the VOIP. This was locking the /media/internal, since it was checking every 10 secs and respawning the service if it's killed, which the mount.sh was doing when going into usb mode.
I'm back to normal - removed the linphone and the log file that was 165MB! without even using that app at all.