I'd say no to the DB Outlook and no to a new MTB if you are on a budget. For $100-$200 you can buy an XT equipped 90's MTB with a nice frame in surprisingly good condition. If you have some patience and know what you are looking for you can pick up a bike that you could part out immediately and make a profit. You can ride it for a year or two and sell it for what you bought it for, or possibly still break it down and make a profit.
You can't do that with a $300 modern bike. You buy it and it's value immediately goes down. You ride it a few times and it's worth $100. In a couple years it's worthless and starts to cost you money in maintenance.
The appealing thing to me about the mid 90's bikes ('92-'96 being the 'sweet spot' since by '98 most of the bikes were no longer handmade in the USA) is there were a bunch of aftermarket parts that are still sought after today. The cold war was over and there was an abundance of metal and machine shops looking for things to make after defense contracts were terminated. Bike parts filled a chunk of that gap. Some of those parts sneak thru on eBay and go cheap at times. If you are into biking and can devote time to cleaning up the bike and buying/reselling parts you can 'trade up' and keep parts you like for your newest bike/frame purchase.
BikePro is a great site for IDing some of these older parts. Click over on the left for 'Hubs and Skewers' to see makers of the items with photos, descriptions and prices back in '95.
http://www.bikepro.com/
If you decide on an older MTB solicit opinions with a 'help me find a bike' thread and post your cities Craigslist link for others to peruse and maybe help you find a hidden gem. I'd look for GT, Specialized, Bridgestone, Ritchey, Gary Fisher, ParkPre, Marin, Kona, Klein and several others that are all still coveted by some. Cannondale are sort of parts specific with CODA brand parts, 1 1/4" headsets and weird Headshock or Lefty suspension. Great bikes with a following still and with iconic riders like Ned and Tinker the brand brings back good memories. DiamondBack just never had that 'must have' bike and doesn't seem to have the 'old school swagger' of some of the other brands.
BikePedia has a great list of bikes since '93:
http://www.bikepedia.com/QuickBike/D...x#.UHKfp64ZYUQ
Older bikes aren't for everybody though. These bikes weren't intended to be ridden 15 years and a hard ridden bike is probably beyond it's useful lifespan. Metal fatigues. People don't do proper maintenance. Even lightly ridden bikes are often in need of repair. Any old bike should be stripped down, inspected and rebuilt. Wheels should be checked by a pro. Older MTB's should be ridden with a mindset that you are on an old bike. Riding style should emphasize finesse over force and be XC/fire road/singletrack rather than DH or jumping.