We are up to 5 separate log books since we bought our boat in 1985 (we write smaller than Stu

). I typically enter the data while underway including course and time to the various intermediate points as well as observations. I always write corrected depth information for the various channels we transit. At the end of each leg of a day I record from the GPS trip length, average speed and time to transit. Its fun to compare times from previous trips and see if we have done better or worse. Really good for referring to again in the future, or to help provide navigation information when planning a Yacht Club cruise out. My wife handles the entries for maintenance, pump outs and fuel added. If anchored, we record bearings to objects on shore to make sure we aren't dragging. The next time we go, we already know where the good reference points are.
One time we were on a cruise out and we talking to another couple. We both thought each looked really familiar. Out came both logbooks and sure enough, 2 1/2 years earlier we were on a cruise out together!
I also have marked up my charts with course lines including distances and bearings. If we do a really long ocean trip I mark positions every hour (usually just taken from the GPS as I've gotten somewhat lazy with the hand bearing compass).
I have been using Garmin GPSes (what's the plural of GPS?) for years now. I always download my tracks and save them to the netbook so I can re-upload them via USB and have a breadcrumb trail if we return to the same place. If I miss an entry on my logbook I look at the GPS track on Mapsource and pull the time from that log to enter in the book.
We just recently scanned our logbooks and they are archived on Google Drive with local copies on my desktop at home and the netbook I use on the boat. That was part of a larger project where we either scanned or found the .pdf files for all the manuals (service and operation), data sheets and instructions for
everything on the boat. Anything new that is added will automatically sync to the local copies on the two computers the next time they see the internet, so I don't necessarily have to be on the internet to look something up. I can get to Google Drive with my phone as well. Its nice to have access to that boat data now anywhere even if the paper copy is either at home or on the boat.
Its probably a bit OCD but I sure hate trying to remember something when I can just look it up. Besides, I think my buffer is starting to wrap and the earlier things I used to know are being overwritten with new stuff. I still have a megabyte memory and we're now at the terabyte level.