Shipping and handling for a stroller or a crib when purchasing on the web will kill the deal!
We now have a two year old and we found our best deals at brick and mortar stores. Sign up for Babies R Us mailings either on the website, www.babiesrus.com , or at the store. We got the best deals there when they send you coupons for big ticket items. i.e. $25 off a stroller. Sometimes they offer extra incentives like a free monitor with a $75 purchase either in the coupons they send or in the Sunday newspaper ads.
It takes a little shopping around, but there are good deals to be had!
If you don't mind "pre-used", it's garage sale seaon! I have seen stollers (i.e. $20) and cribs (i.e. $50) go dirt cheap at garage sales in the Chicago Suburbs area. Taking a Friday or Saturday morning to drive around may be worth it! You can also check out www.craigslist.com or yahoo's freecycle newsgroups.
Personally, I had good luck with buying strollers on-line, but like anything you buy on-line, you just have to know your prices. http://www.strollers.com/ has free shipping over $100. I also had good luck and good customer service with http://www.livingincomfort.com/indoor-store-baby---kids-stuff.html which isn't offering free shipping, but if you know your prices, you should be able to get a good deal. Also Babies R Us sometimes offers free shipping too.
If you don't mind a used one, you might check out http://www.freecycle.org/ There area always people getting rid of baby stuff. Just find the closest group in your area.