I am a huge fan of the
Hakko FX888D. Fast heating, accurate and the tips are as easy to source as Weller — I get tips from Amazon, MicroCenter and (recently closed) Fry's.
Haven't used the Weller listed in this thread, but avoid the budget-priced, analog Weller WLC100 station, it uses a set screw for hold the tip on and when it got hot, and it was not unusual to have the tip drop out on to my workspace. By comparison, higher-end Wellers (and the Hakko) have the screw-down cover to keep the tips firmly in place.
As to the drill, the Craftsman will be fine, make sure the bits are sharp and in good shape. But it's not something I would try and do without a drill press, or a p-lunge attachment for a hand drill. You need to have it
exactly square on.