Hi Ryan,
Never broke one either; however, was cautioned over 55 years ago by an elder mechanic that improper head gasket "sequence" over-tightening is the main cause of breaking Model A water outlets.
1. First: The sequence of tightening a head gasket is from inside-to-outside to press or squeeze the head gasket outwards as opposed to inwards.
2. Second: It is important to tighten head bolts incrementally, (especially with slightly warped heads), little or a few foot-pounds at a time. Maybe like tighten all first to 20 foot-pounds, then all to 30 foot pounds, 40 foot pounds, 50 foot pounds, & finally 55 foot pounds.
3. If all are done quickly in recommended sequence, not a little at a time, from 0-55 foot pounds, when re-checking #1 center head bolt for the second time, it may now be at 20 foot pounds, so a great deal of bolt stress was placed on for example #13 on the front end of the head at the water outlet.
3. The sequence for tightening heads recommends that the water outlet gets tightened on the tail end, i.e., #11 and #13 of #14 & which can cause increased stress on these head bolts if done quickly from 0 - 55 foot pounds.
4. Maybe look at it this way:
A. Jack up a house, up high, on both ends first ..... now the center jack will have the most stress when subsequently lifting.
B. And then try jacking up the middle up high first ..... now the two end jacks will have the most stress when lifting.
5. I doubt if "experienced" Ford workers broke many water outlets with Ford's thick copper gaskets ...... and as far as we know, paper matches and silicone sealant were not available.
Hope this helps.