The funny (as in funny sad) thing is that it is really easy to organize in iPhoto and once I have everything set up it will be easy to stay organized. The real issue right now is the volume of photos I have to go through. Here is how I'm arranging things for now.
I only keep a couple of years worth of photos on my computer. All the rest are on a back up drive I can easily access if necessary. I initially created folders for the individual years I have on my computer (plus one specifically for our old house since that spanned further back).
Then I created a bunch of subfolders. I have a House folder and a Life folder and within that I break things down even more. Once I had all my folders set up, I went through each individual event and just dumped the photos in the appropriate folder (no delting or anything). Once all the photos in an event were in folders, I minimized that event (notice that I don't even bother to title them) as an indication that it was finished. Once all the photos are in the correct folders, I go through them and delete duplicates (since all the same type photo are in the same place it is a lot easier to spot duplicates) or bad ones and if necessary, split the photos into separate albums that I can then title for very fast reference.
I've managed to dump all of my 2012 photos and about half of 2011. I'm already feeling better but I'm still a far ways away from actually reaching my goal and I know that if I get new shiny pictures to edit, this will never get done. So please bear with me while I push through and get this finished.