You may need to rephrase the question or issue differently but I think that answer is that you can’t. At least, you can’t have it both ways.
From what I can tell, you may want to use CD track splice markers rather than CD track start and end markers. CD track splice markers offer no space between the end of one track and start of the next.
I typically always use CD track splice markers for album montages but especially for a live recording or album where there is continuous and overlapping audio (or no space between the songs), CD track splice markers work best for me. They’re great because you simply mark where one song ends and the next starts, no concern about negative time and how a CD player or iTunes will handle it. Find the right balance of breathing room before the song kicks in vs. how much decay or air from the previous track can work being on the next track.
I find that each CD player skips to tracks differently, and not always 100% precise. My car CD player for example puts a small fade in on each track if you skip to it, which I find annoying when it’s a live album or a CD track with an immediate start.
When you have songs that run together or overlap, sometimes you have to choose between an abrupt start to a CD track, or having a tiny bit of the previous song included in the next CD track.