Hi Brisbane123, that is a difficult question to answer without having the benefit of understanding the issues.
Ordinarily, a chronology would include all relevant facts in date order and would not be separated under different headings. What I would usually do in a more complex chronology would be to add an additional column which would be numbered from 1 onward, and use that numbering to cross-reference subsequent matters where appropriate (for example you might have an entry on a particular date, which referred to a factual event "Settlement of purchase of house at 1 John Street, Maryland (see no. 485 re refinancing of this property)".
If the amount of material that you want to put into a chronology is so detailed and extensive that you don't think it can be understood without headings, I think you really need to think very hard whether all of the material that you want to put in is truly relevant.
Ultimately it is a judgment call for you to make, but I would strongly suggest that you try to create a chronology that has all facts within it, in chronological order.
Also remember that a chronology is not a piece of evidence, it is really just a tool to assist the court.