Well, it depends. You should be careful, but then what's the worst that can happen? I had a rather bizarre experience with a first time angel investor, who invested the money and then decided he didn't want to spend the time being an angel investor and basically wrote us off as a loss and didn't want to talk about our business. But the money was real and I wouldn't expect my scenario to ever happen to anyone else.

Is the investor bringing anything to the table besides money? You'll want to ensure your investor is mature enough to understand basic things like he is making a loan/investment to your company and that you aren't personally liable for it. Make sure he is an accredited investor. Tell him to go to Angelconf! http://www.angelconf.org/ Hell, maybe you could go with him.

In this economy, if you aren't in the Valley you may be waiting a very long time for smart money. So is it normally looked down on here to take non-smart money? Yes. But if you're not a company coming out of YC that is juggling angel investors to find the one that is the best fit, sometimes you have to take what you can get.

Are you planning applying to YC or any of the incubators? That would be another reason to wait.

At this point we feel we are too far along, and need to much money to go to YC (but, this may simply be us being closed minded.) We are planing a massive relaunch as a push to finalize some sort of series A.

One way of looking at YC is that you give up 6% (perhaps less for you) in order to be able to raise your subsequent rounds under much better terms because of the superior connections provided.