Transitioning photo library from PC to Mac/iPhoto

Question

I am just starting to acclimate myself to a new Macbook Pro, and I'm looking for suggestions on how to handle my photo library from my old PC desktop.  Because of the limited storage on my laptop, my plan is to keep my photo library on an external hard drive. 
All of the photos on my old PC are currently organized by year, then by month (a decade's worth of photos), and I'd love to take advantage of this switch to use keywords, faces, and other features of iPhoto for more specific tagging of my photos.  But, due to my unfamiliarity with the way iPhoto handles its file structure, I'm a bit hesitant to dive in just yet.  Does anyone have suggestions for how I should go about moving my photo library over to the Mac?
For reference, I'm using Mac OS X 10.9.1.

Answer 1

As well as changing from PC to Mac, you're also now thinking of changing the paradigm of how you manage your Photos. What does that mean?
Well this is file organisation:
All of the photos on my old PC are currently organized by year, then by month
You could use precisely the same structure to organise word processing documents, or powerpoints or whatever.
But that file is not your Photo. It is just a container -  a box - for your Photograph. Think of it this way:  In my iTunes Library I have a file called 'Let_it_Be_The_Beatles.mp3'. So what is that, exactly? It's not the song. The Beatles never wrote an mp3. They wrote a tune and lyrics. They recorded it and a copy of that recording is stored in the mp3 file. So the file is just a container for the recording. That container is designed in a specific way attuned to the characteristics and requirements of the data. Hence, mp3.
Similarly, that Jpeg is not your photo, it's a container designed to hold that kind of data. iPhoto is all about the data and not about the container. So, regardless of where you choose to store the file, iPhoto will manage the photo, edit the photo, add metadata to the Photo but never touch the file. If you choose to export - unless you specifically choose to export the original - iPhoto will export the Photo into a new container - a new file containing the photo.
The difference shows best in iPhoto, where you can search on the same things as the file manager, plus a whole lot more, you can organise in many, many ways, effectively and efficiently.
As you want to store your photos on an external then you need a HD, connected to your Mac via USB or Thunderbolt and formatted Mac OS Extended (Journaled).
On that you create a LIbrary and import your Photos to it.
(And you'll need a second one (at least) for back up.)
You can work iPhoto in two modes: one it manages the files and the other you do. Use the first.
For more on iPhoto and file management see this User Tip:
https://discussions.apple.com/docs/DOC-6361
I strongly urge you to import a couple of hundred images to iPhoto and explore first. It's a good app, but it's not for everyone. So get some in and see what it does (and doesn't).
As for organising: Here's a canned answer that might suggest some possibilities:
I use Events simply as big buckets of Photos: Spring 08, July - Nov 06 are typical Events in my Library. I use keywords and Smart Albums extensively. I title the pics broadly.
I keyword on a
Who
What
Where basis (The When is in the photos's Exif metadata). I also rate the pics on a 1 - 5 star basis.
Using this system I can find pretty much find any pic in my 50k library in a couple of seconds.
So, for example, I have a batch of pics titled 'Seattle 08' and a  typical keywording might include: John, Anne, Landscape, mountain, trees, snow. With a rating included it's so very easy to find the best pics we took at Mount Rainier.
File -> New Smart Album
set it to 'All"
title contains Seattle
keyword is mountain
keyword is snow
rating is 5 stars
Or, want a chronological album of John from birth to today?
New Smart Album
Keyword is John
Set the View options to Sort By Date Ascending
Want only the best pics?
add Rating is greater than 4 stars
The best thing about this system is that it's dynamic. If I add 50 more pics of John  to the Library tomorrow, as I keyword and rate them they are added to the Smart Album.
In the end, organisation is about finding the pics. The point is to make locating that pic or batch of pics findable fast. This system works for me.
Finally, as an FYI:
For help accessing your photos in iPhoto see this user tip:
https://discussions.apple.com/docs/DOC-4491