Drill bits

A trick I use to achieve perpindicularily is to chuck up the tap in your drill press and place the work piece in a vise. Hand turn the tap (of course it's hard) while using slight downward feed lever. Go slow and back off every 1/4 turn to dislodge chips. Try to get at least one full turn . Transfer the workpiece to a vise and carefully start the tap, letting it index in the thread. Works for me. Takes some practice. To gain some leverage during the hand turn I engage the chuck wrench which gives some purchase.
I found these device by accident. They are now on my "wish list" !

Big Gator Drill and Tap Guides (Clamping not required for tap guide)

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To start a tap straight you can also drill the hole to the fastener size to act as a guide. This only works if th part is thick enough to sacrifice some material or you can get to the back of the hole. For instance if your tapping a 1/4-20 thread an inch deep drill to .204 then drill down .150 or so with a .250 drill and that helps start the tap straight.
 
Back to holes...Some hand drills have spirit bubbles for x-y which should help. I have even used 90 degree squares as "sight lines" in the background while hand drilling. This alignment becomes a real problem in e.g., wood door panels, or rectangular tubing that must be drilled free hand. Bummer when the bolt heads and nuts will not snuggle properly.

Creating threaded shafts with limited tools is very difficult. I have had some success with the drill press alignment stated above. Extending threads on a thick shank bolt is not so difficult (but threads are weaker), but does not work on rolled thread bolts where the shank od does not support a proper thread depth. That tool above looks very good, and expensive (tool steel?).

Edit. Rummaged and found a handy, low cost drill jig bought years ago at H Frt . Not in the same class as shown above, but handy. Not at H Frt now, but at Amazon and Rockler. It is a plastic base with 6 slip in bushings.
 
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