I tackled this issue a few years back. First I scanned all old photos (pre digital photos) into my pc (I have some family photos from the late 1800s and early 1900s that I am holding onto - Apparently, they can fetch some good money at auction). I have all photos stored online and on a backup drive.
Next I went through all photos (we did print digital photos in the beginning when digital photography was still new, but have not done so in a while) and selectively pulled out the better ones that I wanted to hold onto. I made sure that each photo was identified by date/location/ people if needed. So I have all printed photos stored in photo boxes and have approximately 3 boxes with photos. I want to mention that I am holding onto these for my DD who can do whatever she wants with them someday.
My major project was to take these photos and make books out of them that tell a story. I use Shutterfly (my photos are stored there as well). I have a book about me and my family history. I made one for my DH and his family history. A wedding book for me starting when DH and I started dating through our honeymoon. I then made photo books of my DD which covers each year since birth through college graduation. Finally, I make photo books for each year that covers vacations and important events. In each book I detail where we were, a history behind the places we go, what we did, etc.
What I found is that these photo books take up a lot less room than photos themselves and I can easily find anything because of the dates that I include on the cover of the books
As DH and I cleared out his family's home a couple of years ago, we found tons of photos stored in large boxes, with absolutely no info on them such as dates, places, people. Such a shame, as we destroyed about 99% of these photos and just kept the ones of his parents and him when they were younger (My MIL could never find photos of DH when he was younger because they were just thrown into boxes willy nilly).
Also,for DD I made digital scrapbook pages (printed these pages out) for her starting when she was an infant, highlighting the important aspects for each year. I continued until she graduated college (This is in addition to the Shutterfly books). She regularly looks through these and loves that she has such a great remembrance of her childhood.
Yes, the process took me a long time (several years), but I got great pleasure in reminiscing and deciding which photos were worth holding onto. I even took my old VHS family tapes and converted them to dvd where I edited out the not so good footage and inserted titles/captions (these are also backed up to a backup drive).
~ and if anyone is wondering, I am the "creative" type and take great pleasure in doing these things.