Suggestions for Beginner Road Bike under $500???

I'm looking for the same thing as OP here.

 My wife and I are doing our first tri in spring of 09.  Both of us want to get a bike, but would like to stay within a budget.

 I found a lot of info and great prices on Windsor bikes and Motobecane bikes from Bikesdirect.com and ebay.

 I'm not worried about the assembly, I can do it myself and have it adjusted by a LBS as I ride it.

 Anyone have any experience with either brand?  (a Windsor Willow for my wife and a Leeds for more)

I hate to say it, but even 7 years ago you could not get an entry level road bike for under $500.

$600ish was the best I found.

Look for used on ebay/craigslist as some others have suggested.

Or get a deal by getting a "last season" model.  I had an odd size frame (47cm) and they still had one leftover from the previous season...different paint scheme, 10% cheaper.

Edited to add:  You could also give him a gift card to the bike shop for however much you were willing to spend on the bike so that he could then chip in the rest....

If you end up buying a low end bike to see if you like it, don't bother upgrading that bike but save for a better bike in the future.

I understand the need to be cheap when you aren't sure if it will be something you enjoy so best value is used.  Some shops sell used bikes most don't.

Key to all bikes is good fit and buying one on the internet or ebay is tough as it might not fit even if it is right size by an on line calculator thing.

http://www.javbike.com/Specials.html

not sure how up-to-date it is, but they show many smaller bikes available. 

My wife and I have had a couple of bikes from bikesdirect (we have one of their stores locally).  I've been very happy with the value for the dollar.  I'll reiterate what others have said; make sure you know what fits before you order.

If you or your S.O. are remotely handy, the absolute hands down cheapest way to ride is to find a vintage road bike in nice shape (Craigslist, pawn shops, etc.).  I love to buy, fix up, and sell bikes, and I have several bikes that were less than $40 to buy.  I just bought my wife a beautiful little Bridgestone 400 from the mid 80s at a pawnshop for $30.  It's lugged steel, all of the components (even the bar tape!) were in great shape.  It rides beautifully, and probably only had a handful of miles.

Go to your local bike shop  and see what they have in "last years" modles. When I first started this adventure 3 years ago I pick up a "new" year old bike (Trex1000) for $525 which was a good deal in my area and "she's" treated me real good for all this time. I have noticed prices do vary from area to area so shop around.

Good luck.

Not quite true;  there are some less expensive bikes that have a great frame, but crap components-if you get one of these, it can pay to upgrade the components.  Conversely, there are some less expensive bikes that have decent components, but a crappy frame.  Don't bother upgrading those.

As many have mentioned, Craigslist is a great resource, but you really need to buy locally with CL (for bikes, at least) since you can go and meet the sellerr and check the fit out, and the wear and tear.  Also, shipping a bike can be problematic, especially if the seller is not willing to pack it well.   I've bought all three of my bikes (roadie, MTB, tri) from Cl and gotten quite lucky with good deals and good bikes.  However, that doesn't always happen.

I just picked up my wife's Window Willow (from BD) from my LBS (that assembled for me).

 Basically, they called it a rebadged entry level Fuji that would have ben a few hundred dollars more in-store as a Fuji.

 To me, that is a good deal.  The frame fits her (took care of that ahead of time) and the components are decent to start, and can be replaced as necessary.

 If and when it becomes worthwhile, I'd easily buy a higher-end bike from BD after doing my research on the frame/fit.