Should my boat get up on plane?

Regarding propeller pitch.

Pitch is like gearing in a car.

Less pitch, like a lower gear allows an engine to make rpm easier.  You wouldn't want to travel down the highway in first gear, nor do you want to start off in high.

At full throttle, an outboard should run in a certain rpm range.  If it does not get to that rpm, it has too much prop, diameter or pitch.

If it over revs, it has too little prop, diameter or pitch.

Number of blades are also factored into the equation.

Your outboard should have a propeller which allows the engine to achieve its optimum rpm range.  

If it does not produce the desired speed with that propeller, you need more power.

You can move a freight train with a five hp Briggs and Stratton if it's geared properly, but it will not be fast.