I understand your reasoning and I concur with you to a point... if alkalizing, in any way, we should be aware of our own body's response... and idiosyncrasies.
The following is pure opinion based on my studies, understandings, and experiences.
If I had weak digestion (I did at one time), however, knew I was generally too acidic and wanted to alkalize, perhaps I would choose to do so slowly over time with dietary changes FIRST, paying close attention to my physical response to one change at a time in order to gauge whether the change was beneficial or not. For instance, if I chose to eat a food and that food caused a digestive reaction that indicated too little acid for the foods digestion, I would then choose not to eat that food again until the problem was corrected down the road, or discard that food from my diet altogether.
In addition, I may want to also introduce alkalizing foot soaks, compresses, and/or baths... especially if I suspected a macro-mineral deficiency such as magnesium, potassium, calcium or sodium, taking full advantage of transdermal therapies.
As an aside, I started experimenting with nigari this week...
Trace mineral foot soaks and baths can be introduced as well; clays, seaweeds and various salts.
Another option, once acclimated to all the above, would be to introduce alkalizing drinks... however, I would strongly advise slow and go AND NOT before or during a meal when you may need strong stomach acids for digestion. Another hint with alkalizing drinks is to start with very small low doses spread out over the day away from meals. Too much, too fast will always cause problems in my opinion. In the event one experiences a reaction from too little stomach acids during the protocol, one could take a little extra weak acid like ACV or Lemon juice; this may seem contraindicated when in pain, but trust me it works well.
I had a real issue in the not too distant past while on vacation with the family and eating far away from my normal habits. I chose the ACV over the antacid (I carry ES, BS, clay, and ACV with me on trips)... the ACV went down hard and for a few brief seconds I thought I had made a huge mistake, but a few seconds more and I was right as rain... bloating went away and all was well.
I believe that the above applied conscientiously over time, could eventually correct the HCL production response in the stomach, if a problem existed in the first place and it was not a case of someone eating foods they should not to begin with. This "correction" of course, assumes the individual is ingesting adequate minerals for proper digestive response and process to occur.
Once the body reaches a comfortable balance, alkalizing maintenance should be little more than good foods and liquids, including fresh juices, along with all the other things that go along with enjoying good health like exercise etc.