The FS landing lessons taught me how to land a Cessna...
After that, move on to the DC3...
Once you're confident-ish, I'd say the 777 ...
I'd recommend moving to the Beachcraft Baron after the Cessna. The DC3 isn't a tricycle gear plane and behaves totally differently then the Cessna on touchdown. Plus the Baron is the easiest twin engine to fly, something critical if you want to move to the big iron.
After the Baron learn to fly the King Air. Then try jets, starting with the Lear. Once you nail the Lear try the bigger iron. I like starting small (737) and working up. There's a lot less inertia to deal with.
Get proficient with every plane before moving on. Be able to stick fly the plane (no autopilot), be able to climb to altitude, hold altitude airspeed and heading, decend from altitude (not as easy as it sounds) and finally land the plane. Learn all the controls, displays, etc.
It takes time before you can fly the big iron effectively. Don't rush it, that's half the joy of the game.