I just don't know a song that has "one" chorus with a length that prohibits it to be used in a medley. Yes if a medley consists of ten songs each with more than 25 measures in average there might be a problem...

It really depends on the choice of tunes for the medley. But the way I see it, there is a very small chance to be stopped by the 255 bar limit. How high is the percentage that the average user with the average medley is affected? In at least 80 percent of all medleys there no problem. In at least 80 percent of the remaining 20 (16% in total) there is a creative solution to make it possible. That leaves a (calculated) maximum of 4 percent of medleys that might be affected.

Maybe somebody has a valid example where it does not work.

Desktop; i7-2600k, 8 GB mem., Win 10 Pro, BIAB 2017; RB 2017 - latest build
Laptop: i5-2410M, 4 GB mem, Win 10 Pro, BIAB 2017; RB 2017 - latest build