The TO bearing never moves as far forward as you show in you pic, when the tranny is mounted up to the engine.
The "nose piece" that the TO bearing slides on sometimes gets worn and will cause the bearing to not slide freely. Or sometimes it just gets dry and you need to put a thin layer of wheel bearing grease or anti-sieze on it to keep it sliding freely. Since you have the tranny out, wipe down (clean) that nose piece good, before you lube it up. Don't use anything that would scratch it or gouge it...just a cloth with some brake cleaner will work fine....keep cleaning until the rag is clean, when you wipe the nose piece.