Overall, the layout looks good. Despite that i have a few notes to make, please keep in mind that this isn’t a complete list since i didn’t check it very well.
Yes and no. Tracks next to each other can crosstalk. This depends on the Vd (how much the voltage changes per time), wave impedance between the 2 tracks, other tracks / copper that can be used as a return path, is there a terminator resistor, …
But since you only use switches, i wouldn’t worry too much. In case you experience crosstalk problems (you press switch 1 and switch 2 triggers also), which is very unlikely, you can just sample the switch 2-3 times before deciding that the switch was pressed.
Do you have a 100nF capacitor placed near every power input of every IC you use?
Why do you go for the RaspberryPiPico rather than a normal µC? Seems a bit overkill/overengineering. Well, depending on what you need to do, but since you have only a bunch of switches and a connector, it doesn’t look like you need a lot from a outside perspective.
In case the baudrate to Board1 is high, you have to make sure the traces are done properly and the right wires are used in the cable.
The connector to Board1 looks a bit harder to get to, depending on how many times you have to connect and disconnect this connector. Are you sure you want the connector there?
How many of them do you plan to make?
I would assume SMD would be a bit easier to assemble, but that depends on the magnitude of the amount of boards (10, 100, 1000, 10000?) and who is assembling them.
The schematic is not a layout. There is no reason you have to but Pin 1 next to Pin 2, … I would suggest you redraw RaspberryPiPico schematic symbol, so that the connections to the Switches are direct. Don’t do the Col1-GPIO16, … table, this is hard to read. Draw the RaspberryPiPico symbol so that you can make direct connections and name still the nets. Mark unused pins with the no-connection flag. Use only a single name per net. It doesn’t matter when the symbols get much bigger and don’t resemble anything of the layout, schematic is for readability.