How To Paint this Wood Trim and Avoid Ridicule from Cub Scouts

I offered to help out with the local Cub Scout pack/Boy Scout troop annual Pinewood Derby™ race as timekeeper and "race official". My involvement was to be just with the electronics; I had fixed their race timing apparatus that uses an "electronic eye" circuit at the top of the course and at the finish line at the bottom. I had hoped to also include an RFID scanner for the cars as well, but instead, I've been asked to expand my role and help out a bit more since a pair of other volunteers were hospitalized after an automobile accident.

They need someone to help with some repairs of the derby racetrack and associated infrastructure that is sort of like a parking lot for cars awaiting their turn to race. Of course I said yes I would help, but now realize I've made a awful mistake: I am hopeless when it comes to physically crafting things, and my attempts always look like they've been done by a 3rd-grader hopped up on too much sugar who only used their thumbs.

I'm looking for some advice about how to get some of this wood trim painted. It is 1/2 inch square by about 36 inches long and I am just not sure of the best way to go about painting it. I've been handed a couple of colors of Rustoleum chalked paint and some small 1" brushes. I've tried googling and am just baffled at all the different methods, I hope y'all might be able to help me.

  1. Do I try to paint it all at once or only one side at a time?
  2. Should I hang it somehow vertically by one end or keep it propped up horizontally?
  3. If I try to paint it horizontally and it is resting on two supports on either end, how do I go back and make sure the ends get painted and look the same as the middle?
  4. How many coats is too many?
  5. How to keep runs of paint to a minimum? (and no pools of paint by the side of the wood?)
  6. What is the best way to avoid getting myself covered in paint?
  7. Is there someone I can hire to paint all this instead?

I would love to hear how you would go about this and - really - any (constructive) advice is welcomed. Thank you!