I'm no wiz using the trimmer but I'll try to help as best I can. I usually just dump it onto a spare bit of the TL and trim it there and then move it where i want it.

Firstly though you cannot get events to move in both directions, they'll only move to the right. That's pretty logical as usually the first event starts at 0 and you cannot move anything before that. If your first event isn't at 0 after youdo the insert you can just move the whole project to the left anyway.

Tricky bit is getting EVERYTHING to move together I find.

This is how it's supposed to work:

Turn on Auto Ripple with All tracks, markers and regions
In trimmer mark out region to insert
Clicker either Insert UoTo or Insert From cursor, youneed to hav ethe TL cursor at the point here you wnat to do the insert.

Now I find sometimes on a project with lotsof tracks etc not everything gets moved. Safest way I find is to select everything to the right of where I want to do the insert, drag it to the right far enough to have a big enough gap to fit the new clip, drop it in and then line everything back up. Other alternative is having selected everything to the right hit G to group it all together.

Hope this helps and remember you've always got unlimited Undo. If you've got a long project check carefully after the insert.