Alright, so I bottled last night and here is what I did: First, I filled the tubing with water as I always do, but also tried to get some into the cane. Then pushed the tubing on the cane and gave it a good effort to make sure it's on there as far as i could get it. When I started the siphon, it went pretty well, had some air bubbles but the flow seemed a little better already. I then followed the trick to squeeze the tube and that worked really well. No more bubbles after that and the siphon went through without issues.
Thanks for all the help!