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In Batman Beyond (TV show), please correct me if I'm wrong, but I think I understand why Bruce quit being Batman: he had a heart attack, but more to the point he picked up a gun which is something he swore he would never do.
But why didn't he tell Terry the real reason why he quit?
The obvious answer here is that Bruce never wanted Terry to be Batman in the first place. When the story starts, Bruce has a hard time trusting Terry, and it takes a long time before he sees him as anything other than a hard-headed teen. After so long mistrusting, it would be hard still for Bruce to explain to Terry his emotions at any point (something Bruce was never known for in the first place). The point with Bruce realizing his mortality, and worse, his desperation in that situation, wouldn't be something he would give away freely to people he cared deeply for. It isn't a far stretch to think he wouldn't want to share it with a stranger, even if he was donning the bat suit.
As for the not so obvious answer... throughout the series, Bruce gives Terry guidance and advice, but he leaves him to become his own Batman most of the time. There are several times we see Terry go for a gun and struggle internally about other decisions he makes. If Bruce told him everything, he wouldn't have a chance to grow into his own man and make his own decisions. Bruce knows the Bat was a means for revenge against his parents' killer and eventually turned into the legend known when Terry takes over. When Terry puts on the suit, Bruce wants him to figure out why he feels he wants or deserves the power and responsibilities for himself.
That's how part one of the first episode goes, but part two and on from there it's contradicted as the show implies some other event scarred Bruce psychologically to the point he hung up the cowl for good- this event is shown in the tv movie Batman Beyond, Return of the Joker (find the original, if you can).
Personal pride. It's not one to admit fault why he would have finally put away the mask for good. Nor would he want Terry to react in a similar situation. While Bruce's sense of honor and ethics made him disgusted to do what he did to save himself; he would not fault Terry using a similar tactic if his life depended on it.
Dunno, but I reckon he didn't want to tell Terry the entire truth, because it probably would have hurt him and shocked him to the core
