I don’t know much about electronics, so any advice would help.
I’m also interested in knowing realistically what the upper limits are for this sort of thing.
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If a Pi Zero-W: https://hackaday.com/2017/03/07/adding-an-external-antenna-to-the-raspberry-pi-zero-w/
All the other models, you can add a USB-based adapter with their own antennas. For really long range, look up Yagi antennas. However, beware there are regulations on antennas.
Why not buy an external wifi adapter with a large antenna? Would be a lot simpler.
I agree with this. And also, if the highest range is your goal, you’ll want a directional (not omni-directional) antenna. Even a cantenna might be good for your use case.