You are very mechanically inclined, so you will likely be very successful in getting your Lee Loadmaster working to your satisfaction. That press does have a reputation among some for being a "beast" to get, and keep, working correctly. I have to feel that a certain percentage of folks have limited/minimal skills with mechanical things, and so are unhappy with the press. I have zero experience with that particular press, so I can't give any first hand evaluation.
Your plan with the Swiss bullets, Unique powder, and Winchester primers should produce excellent 30 Luger ammo.....when you are ready to take the plunge. Handloading is a great, and very satisfying hobby for me.