While I have not had to deal with that particular problem, the way to
start a screw or bolt hidden within a deep recess is to use a dowel to
position the screw. Stick the head of the screw to the dowel with gum/
mastic. it is easier to feel the locating of the screw with only a
light weight positioning stick. A pencil and blutack are usually
enough for small stuff, which is where I'm usually at. With a thin
enough dowel you can also peer down the hole so you can see which way
to jiggle the screw. Sometimes a tubular spanner can be used with
ease as opposed to using a socket and bar. With all the mass of
socketry it becomes impossible to feel the drop as screw locates but
occasionally the use of a cigarette paper to hold the screw steady in
the socket will stop the srew otherwise cocking and failing to engage
the tapped hole.
But you sayd bolt - erm put your dowel through from the nut side
and join it to the end of the bolt, through the column, with gum/
mastic or other tacky/sticky stuff you can imagine. use an extension
bar from socket set to press the bolt through the hole while the dowel
leads the bolt.