Cool tree Mason, and looks healthy, can we see a few different angles of the tree. My only thought is that the barbell branches could be an issue in future.
Regarding what work and when, I would get some advice on needle plucking and removing candles from a local club or a good Bonsai nursery. Most of the candle work is done in Summer and hard chops are done in winter generally speaking... different timing and work will help you achieve different goals on a pine, like ramification and needle reduction, back budding etc... I still got a lot of learning to do myself, pines aren't the easiest trees to work with, but no reason you can't learn right
There is plenty of information on the net about pines but it is important to carry out all the work at the precise time for your climate and area.
Here is an article worth a read by Brent Walston.
http://www.evergreengardenworks.com/pines.htm