Possible new bike.

I always try to get something that is a little more than what I think I need at the moment, with two ideas in mind.  First, if I decide I like something, I will be able to wait longer before wanting to upgrade.  Second (and more rarely) if I don't like it, I figure it will be easier to recoup my investment on a better product.

That being said, I would get the more expensive bike.  You will have more gearing options, and the components are going to be higher quality.  They are still entry level, but on the Windsor they are still lower.

My other piece of advice is to see if you have any biking knowledgable buddies to help you figure out what will work best for you, knowing what you want to do on the bike.

If you can manage, I would go in the other direction and add an extra $30 (on top of the Wellngton 2.0 price) for the 3.0 -

http://www.bikesdirect.com/products/windsor/wellington3.htm

You get Shimano Sora front and rear, which brings it up to the standard of most of the entry-level bikes sold at LBSs that I saw.  You also get a carbon fork instead of Cro-moly which is nice - I found that some LBS bikes don't have that.

It's weird that I seem to have gone through the same things as you... the hybrid etc... but my wife got the 3.0 and has been very happy.  We actually ordered the 2.0 but they were out of her size so they offered a free upgrade.  I recommend getting the LBS to assemble and tune it unless you are very proficient.

Good luck.

I'd definitely go with either the 2.0 or 3.0.  Main discriminator for me would be the integrated shifters (shifters are part of the brake levers) rather than the stem-mounted shifters on the 1.0.  That feature alone is well worth the extra $70.

Threadless stem/carbon fork on the 3.0 is probably worth an extra $30.

You'll also want to upgrade pedals fairly quickly to some kind of clipless--SPD pedals and inexpensive mountain bike shoes can probably be done for less than $100.

I am in the same boat as you and have been looking at a variety of options.  I am far from an expert on bikes but I have been looking at this one:

http://www.costco.com/Browse/ProductSet.aspx?Prodid=11306882&whse=BC&Ne=4000000&eCat=BC|111|195|22170&N=4007944&Mo=6&pos=5&No=2&Nr=P_CatalogName:BC&cat=22170&Ns=P_Price|1||P_SignDesc1&lang=en-US&Sp=C&ec=BC-EC10999-Cat195&topnav=

 It seems like a good deal with carbon fork, Shimano Sora components, of course you would have to be a Costco member but I sure like the idea of dealing with Costco more than Bikes Direct.  If you have problems or just don't like it, they would take it back, no questions asked. 

Also the 1.0 has CroMoly Frame=HEAVY the 2.0 is alum with CroMoly Fork.  I didn't look at the 3.0 perhaps it's all alum which is even better!!!! 

x2 on the shifters as well.  I'm by no means saying you need a $2k bike just don't go all the way down or you'll wish you'd upgraded

Also, I would check ebay and craig's list too.  There are some deals to be had.  Also, I'm sure in Miami they have police auctions.  This is where they sell off bikes that were stolen and not claimed or siezed.  There are some very nice deals to be had there as well.

Somewhere there is a listing of Shimano components by quality...mostly just check that and wieght and you'll have a pretty good idea of what the bike is worth.

I think the order is Tigara, Sora, 105, Ultegra, Dura Ace.  I could be flipped on the first two.

Good luck!!!

Thanks for all the posts.

 I discussed it with the misses and went into my LBS and demanded a good deal, rode a few and decided on the Specialized Sequoia for $500, it rode just as good (for the small amount of time I did ride) as the other more expensive ones I tried. Not as an aggressive position, which is good for starters but the stem can be adjusted to be more aero. All in all I'm pretty happy with it, took it out this morning for a 30 min. ride and definetely noticed the difference between a Hybrid/MTB and a road bike. Thanks again for all the replies.

For the additional money spent on the bike, you got a helluvalot more than you would have with the Bikesdirect.com option ...

Now go ride the new off of it!