I've made a lot of handles for socket chisels, both antique and modern. The antique chisels with the rough interior sockets hold a handle well - I never had one come loose. I did have trouble with the LN chisels which I made new handles for (the stock handles are too short).
Regarding fitting the handle to the socket, there should be small "gap" between the large part of the handle and the top of the socket. Over time, as you use the chisel (and pound on it) the wood will compress and the handle will go further into the socket. If you don't leave a gap, the large part of the handle starts to mushroom, or the handle gets loose.
Mike
Go into the world and do well. But more importantly, go into the world and do good.