Note: I am still a student pilot. Is this knowledge just something can comes with experience, or do I need to buckle down and start studying harder?
Both.
Being able to answer any question on the oral test regarding the stuff you don't have much or any experience with (airspace and FF stuff is a common weak area, it's not just you) will rely mostly on your studying of the regs. But showing you understand how to smoothly deal with ATC-related items in your local area, where you will take your check ride, will come from flying in that area.
As if you needed more tips, here are a few that helped me:
-Ask your instructor a lot of questions about airspace transitions, etc in your area, and ask to do some dual flights that involve that. Or bum a ride with an experienced pilot, and have them show you how they do it. It's not that the regs are different in practice than in the books, but there are nuances. It's a lot like simple "radio fright"... you will get over it by just doing it.
-If passively absorbing stuff from books and videos is not working efficiently, try flash cards. I made mine myself, jotting the questions down as I studied, and just kept working through them, pretty much every day. Chart symbols, runway markings, light gun signals, stuff from the training aircraft POH, and all the airspace, weather and pilot regs that were relevant. I also took notes during ground school, and worked that stuff into the mix. I even used the cards to train me to remember what FAR part or POH chapter was for what topic... the oral will be "open-book", but you will "score" better if you can thumb directly to the correct parts of the books if you need to look something up. After a while I could get through the whole pile of cards without getting any wrong. Then I kept doing that, whenever I had time, including just before the written, the oral and the checkride. They made a huge difference for me. I had a lock on that stuff when I went in for the written- would've aced the written if I hadn't ticked off one wrong multiple-choice answer by mistake (knowledge does not equal intelligence, LOL).
I am convinced that a big part of my success with the cards was that in writing the stuff down, and formulating the info as questions, I got it embedded deeper in my brain, in a more organized way.
-Rather than start sweating the written right now, try a few mock writtens. This will make the real thing much easier. You will see quickly where your knowledge is weak. Like the flash cards, take practice tests often, until it becomes a routine thing. I can almost guarantee your "game" will improve if you just incorporate this kind of study into your life, instead of trying to force the stuff into your head.
- Same goes for the oral. Practice taking it. Have your instructor, or any pilot you know, try to stump you, reading from the FAR/AIM, with material relevant to the PPASEL oral. This could even consist of you and another student, each with a copy of the FAR/AIM, reading questions to each other. Again, playing the teacher can make you a better student; you see the information from a different angle.
-I would NOT advise asking any old airport bum to feed you info direct from their memory... it will likely be outdated or just wrong.
Don't really know why. 
