Recommended bike upgrade?

If you are looking new,  Bicycling magazine just raved about the Giant OCR3.  I think it is about $650.  Also a few months ago they rated the Trek 1000 as "best bike under $700".  The trek has a Womens version too.  I test rode that felt f90 and it was a sweet bike.  But it was $690 normally.  Wait till end of season or start of season sales and you might find something under $600. 

Used is often a good option.  Problem is you have to wait for a good deal, on a good bike, and it has to be the right size.  Seems like it never happens for me that I find all 3 criteria. 

Another option, try renting/borrowing a road bike and see how much difference it makes.  Maybe it isn't as much as you think. 

Nope. Usually in September/October, dealers try to liquidate old inventory in order to order new models in time for the Christmas shopping season.

The other thing about the fit, is make sure the "salesman" is really checking your fit.  Some LBS are horrible at making sure the bike fits YOU.  They see a commission check coming their way and could care less IF you ever come back.

When you go wear your bike shorts, make sure they understand you will be out for a 10-30 minute ride.  Most shops that WANT your business will have no problem with that.

Check the papers, one of our LBS had last October a 10% off sale.  Once you find a shop and a bike, if they aren't listing a special ASK.  They might be willing to knock something off the bike.

I ride a Trek 1000 that is 4-5 years old now, someday I will upgrade to a Tri-bike, but not likely in the next 1-2 years.  When the 10% sale comes around this year, I am planning on getting a mountain bike.  That way I can off road with my kids.  Skinny tires get stuck in the mud!