The almighty steelhead

Let me start off by saying, I know that I ask a lot of questions, but I really appreciate the help you guys are offering.

I am a new fly fisherman and have decided that I want to try my hand at catching a steelhead this winter. I went to the local fly shop and figured out that I can get an Echo 9′ 8# rod for $100 and an accompanying reel for another $100 or I can buy the basic beginners kit for $180. I think I will go with the two separate purchases because they are of better quality.This shop also offers casting classes which I figure I will end up taking sometime between now and going fishing. Now onto my questions:

TIME: I have heard that winter steelhead run between Dec. & Mar.. Is there any particular month where the fishing is better?
LOCATION: I have heard about the Wilson and Clackamas river. I do not want to travel too far but am willing to go out to Tillamook. I live in SW Portland. What rivers are good choices? Not looking for any ones special spot, just some pointers.
FLIES: Obviously, knowing what flies to use would be important. I like the idea of swinging flies, rather than nymphing, but am not opposed to it if you want to persuade me.
WEATHER: After doing some googling it appears to me that this is the situation: Wait for a period of steady rain to fill the smaller rivers, then wait for a few days for the mud to settle. OR fish the big rivers but have to wait for possibly a week for the debris to settle. What are your thoughts?

GUIDES: Does anyone know of a guiding service that is not ridiculously expensive? I have been looking but it seems like any steelhead guides are running $300-$450 A DAY. I don’t know because I have never done it before, but that seems a little ridiculous to me.

Again, thanks for your help guys.

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