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05 TTR 230 oil change problems

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I picked up this bike last weekend and started doing a little maintenance today but ran in to some trouble on the oil change..

First thing, when I try to drain the oil only a few ounces come out. I can close up the oil drain run the bike for a few seconds and roughly the same amount of oil will come out again without me actually adding any oil back to the engine, I tried this because the oil indicator still showed good on amount of oil after doing this about three times... Is all the oil suppose to drain from the plug on the bottom of the engine? It doesn't, so if it is what the F?

There seemed to be a lot of metal shavings on and around the oil filter. Normal?

When I put oil back in to the engine, it only amounted to probably half a quart (oil was between the "max" and "min" lines) and couldn't get any oil to come out of the bleed bolt. So I added about another half a quart and some started spitting out, but just a little, is that what I want it to do or should it be "squirting" out of the hole. I looked over the oil filter very carefully to see if it matched the old filter and it does. Right now the oil indicator is way over the "Max" limit but oil is coming through the bleed bolt hole..

I also noticed when watching the "oil window" when I start it the oil doesn't immediately start "flowing". It looks like it's not doing anything and then after moving the bike around and watching the window the oil will begin to flow toward the bottom of the "window".

Am I just being paranoid?

I am fairly mechanical just never messed with engines this big. I also have the user manual and have looked to it for where things are located, such as the oil filter, and what it recommends for oil and stuff but it's not all that informative on actually doing anything to the bike.

Thanks in advance!

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Remove the big drain plug and spring on the lower left side. After draining, refill with one quart. That's how much it takes, regardless of the sight glass. The window gives unreliable readings, I think.

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