anything is possible, but you will have to understand which one is which.
1) Wiring issues, no issue at all. Whether is it a pickup with 2 wires(single coil) or 4/5 wires(humbucker) coming out from the pickup, it is not an issue. Any guitar tech that charge others money for working on the instrument, should and must know what to do. This, you wont have to worry, just pay the guitar tech and let them do the job
2) Swapping different sizes pickup. The measurement/dimension of the physical size of the pickup you want to swap are different. It wont be a straight, drop in and wire it up process.
With the swapping of a different size pickup, either theres a need to "dig out" more wood from the guitar or "filled" up the excess space in the pickup cavity in order to fit the new pickup. Some of the pickups you have mentioned, in general are really obviously different in size, so it wont be a straight, drop in and replace process.