I don't have _any_ experience with imperial threads, as we use 95% metric here. I've invested a fair amount in a range of metric taps and dies of good quality from 3 to 12 mm, and all the standard metric taps have freely available drills for correct sizes. Also,nearly all of the taps I have come in sets of three progressive taps. It may be a PITA to use the successive taps, but so far, I have not had an issue with getting taps stuck/broken (touch wood!). I follow a few simple rules:
Clean taps before & after use.
Use a good tapping lubricant suitable for the material you are tapping.
If at all possible, drill & then tap (manually!) in the same machine immediately after drilling. If this is not possible, take the time and make a tapping guide to help you tap when not in the machine. Right now, nearly all of my tapping happens in either the lathe or the drill-press. I drill the hole, then replace the drill-bit with the first tap, and using minimal pressure, feed the tap into the workpiece (or workpiece into the tap - depending on what I am doing), until I feel it just pressing against each other. Then, by hand, I turn the chuck, still maintaining a minimal force to start the tap. after a couple of turns on the chuck, it becomes self-feeding - so I thread to depth. To reverse, I just reverse the minimal pressure (on the lathe this is a full reversal, but on the drill press, it is using less pressure, as it is self-reversing), and turn the chuck in the other direction. I keep minimal reverse pressure until the tap is free of the workpiece - everything happens pretty much by 'feel'. Same story for each progressive tap - they take up the previous thread nicely doing this. This method leaves a tiny bur sticking up at the start of the thread once the last tap has been used. I normally remove the bur by just using a countersink in my hand and turning it "into" the thread. Makes for a nice and sure-start thread every time.
The only metric taps I currently have that don't use the three progressive taps are for 10 and 12 mm Metric Fine - they have only 2 taps each. I nearly had a fight with the salesman when I first bought the 10mm set; I accused him of trying to sell me an incomplete set! The reason is simple though - the metric fine requires less material removal to cut the thread, so only 2 taps are needed.
Also, another observation: A metric tap normally won't screw into a die. Besides for the difficulty in trying to get the them screwed into each other because of the gaps for the cutting edges, the nominal OD for a tap is larger than the nominal OD if a die, and a die has a smaller nominal ID than a tap.
Hope all this makes sense ;D
Arnold