Starting off, WOW what a great community to respond so quickly with no trolls or sarcasm. For that, THANKS! Ill get right to some followup questions I have:

1) The http://www.trekbikes.com/us/en/bikes...rdtail/marlin/ looked nice, but I could only find it at the $599 price point. This would put the bike itself too expensive as it's the top end of my spectrum and I would still need some accessories to go along with it.
2) I'm 5'11'' so that would put me in the catagory for the 'great buys' and i oh so love the sound of that. Was the Schwinn Trailways the only bike you could think of that fit that great buy catagory? In addition, I dont think I'd need all the accessories you listed just jumping in for the rest of the summer/fall. Maybe some of these things I could put off until I can recoup some funds after the initial purchase What accessories would you recomend first? I hate to even post this, but cosmeticly I'm not too fond of the rack on the back, but it's something I could probably get over.
3) The Specialized Crosstrail Sport looked really sharp but again the $580 pricepoint is going to be a little high with accessories. It was mentioned that each year new versions are coming out and the previous generation drops in price. Will this be true with the crosstrail sport? Secondly, is it worth looking for a used bike? It may be the only way to fit this one into my range.
The rebutle from meanwhile has me a little timid though... I didnt understand the whole thing but would the crosstrail be suited for hills, offroading, and road as a stock bike without any specialization? Money is a major factor...

Thanks again guys for all the input and any more would be highly appriciated... I'll be out shopping at my local bike shops soon and this has been a great tool to help guide me along. I want to stay away from a department store when picking a bike, but it seems that may need to be a possibility as most quoted bikes were on the edge of my budget. Until next time!