I am usually against double posting but this would probably require a separate post.
First, a description of the mechanical side of titles as they are now. There is a set series of priority for determining which title appears in your message. I will refer to them according to tiers, with lower tiers being covered up by higher tiers, and equal tiers coexisting. For tiers with the same number but differing numbers of the ' symbol, it means that the ranks function in similar ways, but cannot coexist.
Tier 0: Outlaw (I think, I have never done much with my only outlaw noble.), appears as: (Outlaw)
Tier 0.5* Commoner only rank: Freeman, prioritizes over T0, appears as: (Freeman)
Tier 1: Noble, including Imperial Knight, appears as: (Noble)
Tier 2: Knight of region, appears as: (Knight of <Region>)
Tier 3: Lord without region, appears as: (Lord)
Tier 3': Duke without region, appears as: (Duke)
Tier 3'': Royal, appears as: (Royal)
Tier 4: Priest, appears as (Priest of <Religion>)
Tier 5: Lord of region other than city or stronghold, for example under classical system may appear in one variation as: Baron of Landmass
Tier 5': Duke of region, for example under classical system it would appear as: Duke of Cityplace
Tier 5* (Coexists with all other Tier 5, overwrites all under Tier 5, but Duke and Lord are exclusive for one character, hence the special tier): Ruler, General, Judge, Banker, Ambassador, Marshal
Any corrections, please point out.
This tiering system appears fairly deliberate as well, indicating the possibility that there was thought put into the priorities of how titles would be handled. In a way it makes sense. Why? Let's go back to the checkboxes suggestion. I think we are lacking some key thoughts there.
1. What would the default be in case the player doesn't hit any checkboxes? Do not underestimate the importance of this, as human laziness has a very high limit. Are we going to default back to the original system I described above? If so, then just how many people would actually use it? Care about it?
2. How would multiple titles be handled? If it's freeform, then there at first seems to be no problem since there are some people who are almost every council position, a duke, a marshal, and an ambassador. But now add to that, what if the guy was also a high ranking member of his religion like an elder priest? That's possible to have nearly all council positions, region lordship, ambassador status, marshal or army, elder priest. Let's add to that all his guilds, shall we? Let's say he's in about 10 guilds because he travels the continent seeking to buff his titles. What would we see then? Here's an example:
Letter from Pompous Longwind
Hello.
Pompous Longwind
Emperor and Judicator and Commander of BigHead, Duke of Arrogantville, Marshal of the Cocky Jerks, Infinity Priest of Narcissism, Almighty Master of Keys to Success, Chairman of Adventurer Beaters Anonymous, President of Ham Sandwich Makers, High Commander of Armchair Generaling United, Prime Secretary of Hedonistic Guild, Manager of Inflated Ego Company, Supervisor of We Are Better Than You International
You get the idea.
Now if we were to set certain parameters, like force them to select political, military, economic, religious, guild, titles, that would still not allow someone like a military dictator show off that he is marshal of an army, or a theocracy leader show that he is both priest and ruler.
The end result is that under a freeform system, you'll have at least a couple players think it would be funny to make their titles longer than their messages. Under a stricter system you will have people complain about how restrictive the choices are. Under the current system you have people like Draco Tanos intent on getting some form of the above two choices or another variant implemented.
Like I said about the Magic Scrolls Feature Request, no matter which way you slice it there will be problems, and there will be visible complaint. Now the question becomes which way would leave the fewest people complaining and keep the most people interested.
