I know EXACTLY where you're coming from. My switch to Mac a few years ago had its fair share of ups and downs. You don't know where everything is and stuff just seems so alien... Trust me though, coming from someone who uses both Windows and OSX, I know the capabilities of the Mac in terms of file management far exceed that of any version of Windows... Everything's just so uncluttered.
To answer your question though about a Decent Media Player:
iTunes is great for every basic aspect of media management, be it songs or videos. Just drag videos and MP3s into it and you're up and running. The tagging-everything-correctly will be a chore, I assure you, but the fruits of your labor will be realized immediately after. Once you transition, you'll never look back and wonder why it was never like this on your Windows machine.
There MAY be other software solutions out there, but it boils down to what you want it to do for you exactly.
My advice is to stick with iTunes for your media management. It'll take a little getting used to (like moving to a new city that has a different culture), but once you get the hang of it, but you'll learn to love it, I'm 100% sure on that. Even Windows users have iTunes on their machines. If that isn't enough reason to justify the hours of updating tags and transitioning media, I don't know what is. Just think of it as moving to a bigger and better home. You just have to get your stuff out of the boxes and into the places they should be.
Congratulations on your new purchase... Believe me, you didn't pay "too much." You just bought a product from a brand that has some of the highest resale values on Earth regardless of how old it is. This is going to be completely off topic, but if you get an HP or IBM machine for $1,000 its resale value after a year will plummet to about $400 to $500. That's a 50% decrease. I bought an iBook in 2003 for about a grand and was able to sell it last year for about $550. Yes, a 50% decrease, but we're talking 4 (FOUR!) years later, Jaymils83. =)
