A couple of points about sockets
Bear with me a bit, because this is about mounting electronic assemblies on top of each other, not necessarily model railroad objects. But it should still apply. My first recommendation would be to run a cable from the tracks and any lighting down through a snug hole in the roundhouse floor through a larger hole in the supporting surface. The hole in that supporting surface should be large enough to allow about 1 inch on any side of whatever connector you attach to the cable. The roundhouse should be large enough to cover that hole anyway.
If you insist on using pins fitting directly into a socket under the roundhouse floor, consider this: When you start stacking things together and there are connectors that have to mate to make them work, one thing that is going to happen unless you take steps to prevent it is mashed pins. This can happen when sticking a printed circuit board into an edge connector, it can be sticking a chip into a socket, it can be when seating a small board onto a larger assembly.
I'm going to skip the "If it's possible to plug it in backwards, it will happen" scenario because something like a roundhouse is going to be pretty tough to inadvertently try and set back on the layout backwards. :D
Anyway, the more pins there are that need to go into a socket, the more sockets involved, and the larger the object being added compared to those sockets, the more likely somethings going to get bent. And you only need one bent pin to really mess up your day, especially if you don't find that out until you apply power. This is commonly referred to as "Letting out the magic smoke" or "The blue flash test", but I digress.
If you are going to try and mate something large like a roundhouse onto something tiny, like a socket somewhere underneath it, make sure that you have several guide pins to key the object into the exact orientation and position over the socket. My suggestion would be to drill 4 holes in various accessible points in the roundhouse interior and on through the supporting surface underneath it, then glue short lengths of brass tubing into those holes in the surface, flush with its top. Fit pieces of brass rod (or tubing) that fit exactly into those lower pieces of brass tube, making them at least 1/2 inch long so that they ensure everything is lined up before the pins under the roundhouse make contact with the socket. Slide those pieces of rod or tubing into the roundhouse floor and the tubing in the surface below, then carefully epoxy them into place. This will give you your guide pins.
As far as the sockets themselves, my suggestion there is that you cut out a couple ties in the track at the back of each stall and make your opening for the sockets in the roundhouse floor. Mark the spaces on the supporting surface, then remove the roundhouse, install the bottom sockets flush with the supporting surface. At this point, slide the roundhouse back down in place, add the wires to the proper pins for the connector to each stall's socket, and push the connector down so the pins seat into the socket. Finish up by gluing the connector in place to the roundhouse floor. Let everything set up solidly before pulling the roundhouse up to remove it.
Again, from my experience as an electronics tech on the bench, the more pins that are being aligned and connected, the more likely that without a very solid set of alignment pins, you will have bent pins, and the more force (within reason) is going to be needed to seat or unseat those pins when installing or removing the top object. Once more, this is why I'd personally use a cable with a connector feeding through a larger hole in the supporting surface rather than mating the connectors directly from the roundhouse floor to the supporting surface. If you insist on mounting some sort of socket to the floor of the roundhouse, then my next suggestion would be to mount all the connecting wiring from your power and lighting busses to cables that could plug into that socket through a larger hole in the supporting surface.
Hope this helps.
Janet N.