Hi Neal, I have no direct experience with the Back Roads Ontario Maps and i wasn't at Lee's lecture but I may be able to help you anyway. The preferred way to buy or obtain from free open-source maps is to get all the maps you think you will ever need onto you computer first. This way you can pick and choose what maps to send to you GPS for any trip you are planning and quickly load them before you go. Any of the memory chips you mentioned will hold plenty of maps and you probably will never need to load most of the maps into the GPS anyway but it's nice to have them on you computer ready to grab if needed. The problem with buying the maps on SD cards already loaded is as you describe, how big should the chip be and what maps will I need has to be sorted out before the purchase. Some people will think that they can do everything from the GPS and not have to use a computer with it but this is just like having a digital camera without a computer. it can be done but it really is not the way to go. the best way to enjoy an organized GPS ride is to dump all your recorded track-logs, your tracks, way-points and routes into you computer and delete them from your GPS before you show up for the ride.
You don't actually need any map in your GPS to ride the boogie but it's nice to have. Assuming you plan to do one of our 3 Dual Sport rides, bring your GPS to the registration on Friday night or Saturday morning and I will connect it with my laptop and load a set of tracks and way-points into it. I will also explain what each track is for and answer any questions. The way-points I provide are for gas stops, lunch, start/stop locations and photo ops. For this, and most GPS rides, a map in your GPS is only there as a background image that puts the tracks in context by showing all the roads and lakes on your screen. A map is still desirable because of the other information like restaurants and gas stations that it contains and if needed you can ask your GPS to plot a route to one of them and this is where the "routable" map does its magic by showing you turn by turn instructions and calculating the shortest way etc. The tracks I provide are a high-res squiggly lines that you simply follow by keeping your bike on the line. If you prefer, you can activate them with the "GO" button but this is optional. A lot of what Lee taught you is not applicable here since his Rally Connex rides are based on Routes not Tracks. Don't worry Tracks are actually easier to use. I wrote some GPS setup instruction appropriate for the boogie here
viewtopic.php?f=24&t=2492.
P. S. The Calabogie Boogie trail ride does not use GPS at all but if you bring one you can record your adventure as a track-log and look at it later. Please be advised that there are several places on the trail ride where we have special permission from land owners for the event or have payed a fee for a day-pass so don't assume you can just re ride it anytime you like.
Cheers,