If it is stopping due to the trigger being too big, you should try to reduce the size of it anyway you can. Honestly. in my opinion having one large trigger isn't a good idea. Comment can help, but having 1-3 or so triggers that do different parts for one thing can really make it easier on the eyes and keep your Trigger Editor organized.
Also, there are ways to reduce the size of a trigger. You may be over thinking what needs to be done to pull it off. When I started working on Dark System for Generic Code. I reduced one of the triggers they made before I joined from 25 If Statements to 0, then added a loop. Things like that can really make a significant difference.
Also, lets say you made 1 massive trigger and then going into the Test Document and all it tells you is that there was a Dialog Parameter Error in a trigger that has loads of Dialogs. That would be a huge mess of not knowing exactly what went wrong. By splitting it up into multiple triggers can make it easier to figure out where errors are happening a much easier process.