It is worth saving to get a good one. Of the good ones, my only experience is with Kool-Stride, which we got after extensive shopping among the brands. I was wonderful, but the other top-end ones are good as well. We went for the Kool-Stride rather than Baby Jogger because it was better for a tall runner (me) and was more collapsible for transport. It's been 5 years, so these considerations may have changed with the models...

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Much like good shoes, you need to test run with the strollers with your kiddo. We bought a medium-end one for little DS, then upgraded to a used high-end one (BOB Ironman) when DS outgrew the original. That said, it really depends on how often you plan to use it, etc. We have put an average of 30 miles per week on ours since we got it and find the BOB to be fantastic--MUCH better to run with than the previous medium-end stroller.

We went to a bigger town a couple of hours away and "test drove" a bunch, then bought ours on eBay. Also, make sure it fits in the trunk of your car... Have fun!

You might also consider getting a used one. We were stunned at how much the new ones cost! We found a used Kool-Stride for $70 and it was in great shape! It's light-weight, has a little storage pocket and a top/roof thingie you can have over the kids head or not. We don't have the rain cover, but I probably wouldn't drag our daughter out to run in the rain anyway. Good luck!
Sue