Yes. Yes. A little oil will help the tubing move easier. The diameter of the tubing needs to be slighter larger than the vacuum hose. May be safer to remove the hose and fix off the vehicle since by now it's certainly not as pliable as when new and excessive movement/force could cause it to bend/break. Honestly, I would ditch the plastic vacuum hose(s) altogether and use the silicone tubing. Air passes through those lines and it won't hurt a thing. Those quick connectors are for easy removal/ replacement, aesthetics, and something else to purchase when they break.