I'm married, have a 2.5yr old, and another kid is expected this summer. I'm mainly a pleasure bike rider, but I've been trying to do more and more. My wife isn't really up to much biking right now, as she is 6 months pregnant. Even when she isn't pregnant, she tires out after 4-5 miles or so. Currently, we've got a cheap inStep double trailer that we were given by my sister for free. It's served it's purpose, and certainly carries kid behind me safely. My dilemma with it is that I'd like to be able to bike somewhere, detach the trailer, and convert it to a stroller. For example, there are tons of places that I can take my son on day trips via bike, but when I get there, I want to 1) Have the option of pushing him around instead of walking with him. 2) Not leave things in the trailer unattended (helmets) while we are off galavanting in the zoo or whatever. 3) Use it as a stroller when going on vacation with our bikes. (I know the stroller function isn't as good as a regular stroller, but when cargo space in the car is an issue, I'd rather bring a multi-tasker than have to bring a trailer and a stroller).
So I've been looking at Craigslist for a used bike trailer that has the stroller conversion kit. Most of the ones I'm seeing are garbage. The inStep trailers are cheap, and some do have stroller kits, but it's a pretty cheap trailer. I could probably pick a used one up for $50-75 fairly easily. I could see some benefit to getting a stroller that is a little easier to pull, and/or more durable. I keep stumbling upon people selling used Chariot or Burley trailers for $3-450. Part of me wants to just buy the more expensive used trailer, since the odds are good that I'll be using this thing for 5-7+ years, and the nicer it is, the more likely I'll be to use it. Plus, the expensive trailers don't seem to take much of a hit with depreciation. In other words, I should be able to sell the trailer for most of what I paid for it when I'm done with it (assuming we keep it in decent shape). It's just that whenever I think about spending several hundred dollars on a device that does little more than what I already have, I want to punch myself in the face.
Any thoughts/recommendations? I'm certainly up for other options.