Don’t be embarrassed. My friend Has an OL arm. I helped him set it up and I must say it is a royal PITA! This is from another forum discussion about that arm!
If you are tracking within the recommended range, you are not too light. Do not exceed the recommended tracking force. The recommended tracking force is not only intended to minimize wear and damage to the stylus, cantilever, and suspension of the cartridge, it should minimize issues with record wear. The recommended downforce puts the signal generating elements of the cartridge in their proper orientation when the record is being played--to high a force pushes the generating element out of its proper location and this will adversely affect the sound. Do not adopt a "cure" for one problem that causes another.
I use AudioTechnica N145 cartridge that tracks at 1.25...1.50g. My cue lever is slow enough to land PERFECTLY without jumping even on records that have thicker lip. That's on my Thorens TD125. On my VPI turntable I prefer to land needle first then turn on motor. It picks up speed almost as fast as DD turntable.
aside from other considerations, suppose everything is absolutely correct:
some cartridges are 'low riders', meaning the stylus cantilever is very close to the bottom of the cartridge body's underside.
thus a low rider bottom of it's cartridge body may still be in contact with the raised edge of the LP, UNTIL, as you describe, it 'moves in' a few grooves, thus no longer being 'pushed up' by the raised edge, (thus allowed to drop down properly into the groove).
i'e. I bought a Wayne's Auto perimeter ring, it's outer edge is thin, yet up a bit from the grooves. My cartridge body is unable to get low enough to play the beginning of the 1st track, until the cartridge body moves in enough to get down enough for the stylus to get into the groove properly. My Sumiko might work, it has a much larger space from the stylus tip to the underside of it's cartridge body, I guess I could call it a 'high rider'.