I'm exploring a few question about the subject:
First is the sulfur in fertilizers the same type of sulfur to acidify the soil. Several elements come with a good percentage of sulfur like manganese Temagtan. I use sulfur coated urea. Would that acidify my soil over a period of years?
Carlos, the sulfur found in fertilizers is a sulfate form and yes, it might lower the pH. If it's not stated on the bag, recommend you call up the manufacturer and find out the CaCO2 ton/acre equivalency. Anything over say......800lbs. is gonna be acidifying with an azalea food around 1,200 lbs.
It's my understanding that sulfur coated urea is acidifying. Again, a moot point IMO as calcareous soil has a powerful buffering affect..... plus it all depends on your rootstock's nutrient uptake profile which is really what you should be focusing on. Attached is chart showing that your choice of WI rootstock, Waldin, should have a low potential for Ca uptake (and N). I've looked at your photos and see no indication of chlorosis. Tissue analysis looks pretty darn good too.

Second: too much of anything is bad. In my tissue analysis there is a line for sulfur and it can test high meaning it will have an adverse effect on the trees. I'm attaching the last test results so you know what I mean.
Not sure what that means. Adverse, how? As in nutrient antagonism regarding other elements?
Third: I doubt we can add sufficient sulfur in our rocky soil to have a meaningful effect.
Yep. There was a fellow who was determined to grow apple trees in calcareous soil near me, so he brought in huge tankers of sulfuric acid and broadcast it using large booms. It was a short term affect and of course ridiculously expensive. He gave up.
Fourth: Is there anything that can be applied with the irrigation water?
Sulfuric acid. I use 78% battery acid bought from an auto parts store in 5 gal. bags and inject it with a Mazzei. My use is to help clean out my emitters. My well water is super high in bicarbonates.
Talk to Dr. Mark McFarland at TX. A&M. This guy is a real pro when it comes to soil science. Also, I know you have resources in Florida but their testing labs are excellent and cheap too.
http://soilcrop.tamu.edu/staff/mcfarland-mark-l/Good luck,
Mark