I have MS Streets and Trips 2010 and I want to transfer the poi's in it to my TomTom. It seems I need to use the est to ov2 converter (http://garmin.gps-data-team.com/poi_manager.php), but when I do, it gets stuck! I browse for my file that I saved from Streets & Trips and select it while at the poi manager site. Without pressing the "Open" button it immediately shows "sending request to garmin.gps-data-team.com..." and never gets out of that loop (likewise if I press the "Open" button). I'm using Firefox, but I tried it in IE without any luck. I have disabled the pop-up blocker and disabled Adblock PLus.
I just tried it with a 192KB file and it seemed to work. However......it showed up another issue I have that may or may not be related. I exported the original, large file as a GPX file. I then tried to convert that to OV2 format using the POI Manager. When I did that, the manager only saw 3 of the 18 POI's. So I looked at the GPX file using Word. It shows that the 3 POI's are in the file as 'wpt' and the other 15 are in the file as 'rtept'. I assume that means the 3 are waypoints and the 15 are route points, but I don't know what that means - to me they are all waypoints along the route where a stop is scheduled.
I can't advise how your software manages your routes and output files.
I mostly use our http://garmin.gps-data-team.com/extra/ POI Editor. I create my route file as a list of separate POIs creatively named: Waypoint 1, Waypoint 2, Waypoint 3, etc, and load them to my GPS...