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@Tychom
I've only ridden with a trailer once, out in the 'burbs, and I never felt too comfortable with it. I find it hard to imagine I'd really want to ride one through the inner city regularly, even a short distance out to the canal bike paths.
A secondary issue would be that it's not so easy to get on regional trains with that sort of bike/trailer, it would be hard to use for cycling trip. I have similar thoughts about cargo bikes and getting them away from the city.
I suppose though in those cases I/we do have other bikes that could be used and perhaps it's best to accept no bike can do everything.
As #2 just turned 2 I'd see a top tube seat as a very short-term solution, but yeah I've been considering it as he'd definitely like it.
I think what most appeals to me is something like a Yuba bike. I followed one through town this morning actually and thought it looked quite nippy and quite short with good handling. Claims to have quite some adjustability in the seat-post department. Reach would still be a problem though if both my wife and I were to use it.
And it looks like you could probably use it day to day and get away for weekends, that + kids + heavy stuff, then wife + other luggage on her bike.