You found the manual here right?
Pioneer PL-50 Owners Manual | Vinyl Engine
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Originally Posted by devinthedude57 
First off, and most frustratingly, if I don't lower the tonearm VERY slowly when I play an album, it clicks back up and resets to the "cut/off" position. I don't know what could be causing this, but I would LOVE if someone could help me fix it.
Second, the tonearm meets resistance when playing too far toward the center of an album. I can't even listen to "My Girl" by the Rolling Stones from their Flowers LP because it's too far in on Side A. Very frustrating.
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This sounds like the auto shut off mechanism is out of kilter. It's probably a metal or plastic cog attached to the tonearm somewhere underneath and when this reaches a certain point it mechanically flicks a switch which raises the tonearm. If you remove the platter (where the vinyl sits) and have a look at what happens underneath when you move the arm around then you should be able to figure out whats goin on.
The cuing issue sounds like it's part of the same mechanism. Are you talking about the lever or hand cuing? if it's the lever then it could also be a belt that's stretched or cog that's wearing out or something. It might be simpler just to disconnect the autoshut off and learn how to hand cue if that's the case as you would perhaps need to find someone with specialised turntable repair skills otherwise.
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Originally Posted by devinthedude57 
I have the turntable running into a Yamaha HTR-5890. I have to turn it up higher than usual when listening to an album, but do I need a separate pre-amp as well?
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This is totally normal but you are correct insofar as it's a pre-amp issue. Are you comparing it to a digital source you have plugged in there maybe? It depends on the design of the amp but some have controls which allow you to fine tune the input gain sensitivity. Look in the set up menus.
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Originally Posted by devinthedude57 
Any other maintenance tips, or any help in general would be greatly appreciated, and I'm definitely going to check out the Denon DL-110 that has been recommended. Thanks in advance, and keep up the good work!
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The Denon may make the issue of having to turn up the turntable worse as it's a lower output so maybe should think about getting a separate phonostage like the Cambridge Audio 640P which will sound a lot better than an av receivers phonostage.
Otherwise have you reoiled the bearing? this will make things a lot quieter if it's never been done. Remove the platter and clean out the bearing well with isopropyl and cotton buds to remove the old oil. Industrial swabs for cleaning tape heads made out of plastic are actually more suitable than cotton buds if you can find them. I think 3M make them. Then replace the oil with 5ml of synthetic motor oil like Redline or Mobil one.
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Originally Posted by devinthedude57 
I also just noticed that it's running about a half-step too fast as well. (That's one note up, for any non-musicians ) Is this a belt or motor problem, as those are the only two things I could think of it being?
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Most likely a belt problem. Has the belt been replaced? Sounds like it's to tight perhaps?