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I'm imagining getting the kid into the seat then mounting yourself could be awkward
surprisingly not with a weeride. I thought this, and bought a kickstand in advance, but found that if I found a sturdy enough whatever - wall, fence, etc - to prop a handlebar against then the fact that the kid is up front helps to keep stuff stable while you are getting them strapped in. Never installed the kickstand in the end.
Maybe my key piece of advice is use a sturdy, stable bike. I did the skinny frame with 23mm tyres for a little while, but the ride was twitchy and at some times scary. I swapped to a rigid mtb and everything was cured. You want the longer wheelbase and long rear stays for stability, the thicker frame tubes for lateral stiffness and bigger tyres to soak up the poor road surface. Gear it so you don’t have to get out the saddle.
Hamax on the back. It’s all good.