Lightroom :: Renaming Photos On Import From Pictures Folder

I recently purchased a new Canon T5i and have started using Lightroom.  So far I am loving both.
 
I plan on importing into my Lightroom Catalogue all of my photos from my Mac's Pictures folder and from iPhoto and my iPhone and iPad.
 
For those photos already in my catalogue from new shoots, I have placed them in appropriately named photos, have religiously used tags and have renumbered the photos using this type of convention:
 
My Initials_Year_Event Description_Sequence
 
I am ending up with some very long file names. I am not a professional photographer so this is all for me but I want to be able to search for my photos from both within Lightroom AND from the Mac's finder. I am looking for input to create unique but descriptive names but not make the photo names very long.
 
Here is my thought process:
 
1. I am using my initials as I can then search in the Mac Finder and find all photos and movies regardless of extension (e.g. CR2, DNG, JPG, MOV).  My initials are not on other files in my Mac.
 
2. I am using a descriptive name so I can search for the photos for example of "Dan's Wedding" and find those both in Finder and in Lightroom.  The Dan's Wedding photos are in a Lighroom directory called "Dan's Wedding" and they are tagged with Wedding and Dan.  This might be over kill but I think the actual file name is most useful to me when it describes the event.
 
3. The number is of course what makes each file unique.

SO.....some questions.
 
1.  Is putting my initials a waste of time?  I could search in Finder for "DNG, JPG, MOV" but I would get files besides those in Lightroom (assume all of the items in my Pictures folder will eventually be in Lightroom.
 
2. Do I really need a date in the file name given that a meta data search will find the photo's taken date?  I am more likely to remember an event name like "Dan's Wedding" than the fact it happend in "2013 June".
 
3. If I use a date, should I put the year first for search purposes?