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It depends what your goals are and what kind of riding you want to do. That Diamond Back in the pic is a strolling around town kind of bike. It'll be comfortable, but it won't put you in a position where you can put some serious power down, get in a tuck, or be very responsive.
If you want to do group rides you must first decide if you'll do mountain biking or road biking. You'll get the most bang for your buck on craigslist used, or bikesdirect.com new. You need to know just what you want though, and neither will offer much help for fit or service. You can get a good idea on fit from the fit calculators on wrenchscience.com or competitivecyclist.com. No matter how good of a deal it is, getting the right fit is the most important consideration. I'd right a perfectly fitting $600 bike any day over a two-sizes too big or small $3000 bike. A cheap used mountain bike will likely be thrashed, but a cheap used road bike for $300 might work great and just be a little dated.
If you can swing it though, I'd recommend checking out a few bike shops. I wouldn't bother with Big 5, sports authroity, etc. You'll get service and advice. Maybe join some bike forums, too. mtbr.com for mountain bikes, roadbikereview.com for road bikes. Even better, ask your neighbors what they recommend. Maybe they have some spares you could try out, or maybe you can borrow their bikes and ride on your own. You'll learn a lot by getting some decent seat time on an assortment of bikes.
Also...try as many saddles as you can. Most newbies think bigger is better. Not so- it's all about the shape and how it fits you. Most will be a little uncomfortable until you have a few weeks of regular riding though, and then you don't even think about it any more if the fit is good. WTB and Specialized seem to be the most popular brands among my friends.
Also...consider getting a decent pair of bike shorts, baggies if you're concerned with the look. They are SOOOOOOO much more comfortable on a long ride. No undies- the seams are murder. Maybe get a little chamois butter, too, although I usually don't use that if I'm going less than 4 hours.
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