I have read the following two academic articles:
The modal gap: the objective problem of Lessing’s ditch(es) and Kierkegaard’s subjective reply\
by Matthew W. Benton
Lessing, Kierkegaard, and the "Ugly Ditch": A Reexamination
by G. E. Michalson, Jr.
It seems that Lessing's error was that he was considering it "necessary" for God to save us, and paradoxically, not necessary for him to believe it since it was in the past and not part of his personal experience. I'm inclined toward Kierkegaard's side of the argument, but I think he gives too much credence to Lessing and removes reason and historical evidence as a possible basis of faith.
This reminds me of the conversion of Strobel, which was based on historical evidence. I think what Kierkegaard was trying to aim at might have been that Lessing's ditch was emotionally based and subjective, or the 19th century equivalent of "that's like, your opinion man" in response to Lessing. Faith can have many different things as its basis, and reason itself depends on faith anyway.
Anyway, I'm done dragging this thread into off-topic-ness. Unless someone decides to respond, I'm calling it a day. @2PhiloVoid, good discussion, and I learned a good deal about you and your theological positions. I look forward to hearing from you in the future.
I'll try to get a response in on some of this later today or tomorrow.