Just using the pre-loading (which is to say, this plugin's LoadBGM command) will cut out a good chunk of that painful pause. But this plugin has way more to offer than that, of course!
Having the two tracks as separate tracks can make it possible, but it depends on how they're configured. The plugin isn't really designed to jump seamlessly to a second track seamlessly unless their timing is synched correctly - that is, if track B doesn't have any sort of intro portion that corresponds to track A, the crossover won't be smooth. (The tempos don't need to match; that's accounted for. But the number of measures does, at least in the sense that track B has to account for all of track A's measures.)
But if that doesn't work for you, there are also ways to do that by combining them into a single track - check out my example video, specifically the part with the Cymore theme. I initially set the loop points to a short part at the beginning, and then, when you enter the town proper, the loop points change to the proper loop points for the rest of the song. No matter what timing you use when walking over, the music will keep right on playing as it shifts the loop points. That sounds like it best fits your needs?
If that's not a sufficient answer, then I might need more info.