I decided early on I wanted a Bob stroller, and we purchased a used one off Craigslist for $285. Just recently, a friend gave me her (again, used) Bugaboo cameleon. Both strollers have their plusses. I tend to still like the Bob better, but the cameleon also has some great features. But, since the Bugaboo was free and I'm sure I could easily get the $285 back on the Bob on Craigslist, I should go for the free, perfectly acceptable Bug, yes?
Re: XP: Bob vs. Bugaboo
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I would keep them both. I actually have both strollers and now that my son is 2 years old and a little bigger, I prefer the BOB. I also think the BOB is a better stroller in some regards. Don't get me wrong, I love, love, love my Bug, but I find myself using the BOB now more than the Bug. I have found the heavier my son gets, the harder the Bug has become to push, I know weird.
I say keep them both. The BOB has a higher weight limit too so even though the Bug says it goes up to 37.5 lbs, you will reach that quicker than you think. Bugaboo is nuts for thinking a 4 year old can use that stroller, there is no way, unless your kid is really small, my son is in the 30th percentile for weight and I don't see us using the Bug much past 3 years old. The BOB has a much higher weight limit and I think eventually you would regret selling it.
If you get the car seat adaptor, then they can face you.
That's true, but I didn't like using a huge stroller as a car seat frame anyway so we used a snap-n-go for that stage. I think it costs less than most adapters. Then I kept her facing me for another year after she was out of the infant seat.
Strollers are so particular to each user. I think I've had 6 or 7 since DD was born and none of them really "do it all."