Drilling the holes in the bulwarks or "chains" of the vessel is relatively easy with a pin chuck and an appropriate size drill bit. I wouldn't recommend drilling the mast or the bowsprit as this will weaken them considerably. Round turns and clove hitches are much better.
Threading the rigging thread through a hole not much bigger than the thread diameter can be a problem, but take heart, there is a fine trick you can employ.
A word of caution before we start. "Keep your fingers moving and be swift and be bold".
Put a drop of super glue, the liquid type, not gel onto a piece of scrap plastic. (old junk CD's are perfect for many uses) Trail the last inch of your rigging thread into the liquid glue until it soaks in.
Lift the thread clear of the glue and quickly pull the thread between your finger and thumb. As soon as the thread is clear of your fingers rub them together and break whatever bond is forming. I have done the hundreds of times and although you get some glue on your fingers, (which I am sure someone will tell me is highly toxic) I have never stuck them together - yet.
The thread however, as you pull it tight hardens instantly into a smooth stiff needle. Cutting the last fraction of an inch off the end will produce a point which you can thread through the finest of holes. The tip can be re-cut every so often to increase the life of your thread needle.
Incidentally, each knot can be secured with a drop of superglue applied with a cocktail stick.