I've striped high school basketball and volleyball floors down through the years. The flooring contractor or the school supplied the diagrams. On wood floors, no special paint was required. We always used lettering enamels, double coating certain colors. On the rubberized floors a special paint is required. I never did a rubberized floor.
Some places spec'd certain paint manufacturers but when I matched the colors with One Shot and showed them, they were usually okay with it. It gets buried by a clear coat anyway.
If I had it to do over again I would have invested the money in one of the tape machines that lay two lines of tape simultaneously. They have wheels and a handle.
The three point line for high school is 19'9" measured from the center of the hoop by dropping a plumb bob and driving a small nail for a wire to pull the radius. The floor taping machines have an attachment for this. On floors where they did not want me to drive a nail I used a piece of plywood with a protruding machine screw, taping the board to the floor.
I would think any capable sign painter could do the work. It is hard on your knees, so a young sign painter is a better choice.
If a logo involves two or three colors, working off a pounce pattern might be a lot quicker than a stencil, since you can lay wet next to wet with lettering enamels. Sometimes stencils tend to allow leaks, too. Masking tape should be high quality and squeegeed down just prior to painting or it, too, can leak.
I did well at this when the logo required some skill to produce. If it was just lines and nothing else, I was consistently underbid by the guys that did this type of work and nothing else.