Corey, all the Penns I have, 209's and 309's, same with the Mag10,the easiest and quick way is just push your oiler on the "button" in the center of the endcaps, they will depress enough to put a drop or two of reel oil in. On the worm drive, I only use dry graphite dust, oil will accumulate to much "dirt". I have mine thoroughly cleaned by someone that knows how to disassemble them about every two or three years, it's worth it. I'm using reels I purchased new 19 years ago with no problems except having to replace the worm drives and pawls as needed due to normal wear and tear, depending on how much you use the reel, regardless of regular maintenance.
If you should buy a used one, the older models have a screw on the side you can remove that carries a spare pawl, it's printed by the screw, also they have the oval molded plastic knobs on the end of the handle.