I think you are definitely on the right track.

Cub Scouting vs Boy Scouting is exactly why I suggest the guide to safe scouting and the age appropriate activities guide. Many dad's get into Cub Scouts, thinking it is Boy Scouts, and expect the boys to go on a hike/campout miles from any facilities, or go on a multi-day canoe/camping trip along the local river, or ... well, you get the picture, and yes, I was guilty of thinking all of that. When my son was a Tiger I was really turned off by all the artsy craftsy stuff, enough so I almost pulled him out of the program, but the reason I didn't was the simple fact that my son liked it, and that was what was most important. Looking back, and looking at where we are now, I realize many of the reasons why it is structured this way. Still, it can be difficult for dads (and sometimes the kids as well) who expect more of the hardcore outdoor stuff during the Tiger year (or the wolf or bear year). That doesn't mean you can't work with your own son on these things at home outside of scouts tho, that's what we ended up doing. It also doesn't mean you can't have a strong outdoor program, you just have to be careful and be aware of what you can and can't do. See the next point.

You should also be aware of what kind of activities can and can't be done at each level, and at different events. For instance, Webelos are the only ones allowed to camp as a Den, and you cannot do shooting sports at a Den or Pack event or camp out. Just a couple of examples, there are many more you need to be aware of.

Training is good, and you can't really start too early, but just an FYI, there are TWO different OLS trainings that I am aware of. There is an OLS training that is geared towards the Boy Scout Program, and one that is geared toward Webelos Leaders (referred to specifically as OLS for Webelos Leaders). The Boy Scout version is still not bad to have, but it can wait if need be. Make sure when the time comes you sign up for the right one.

Keep up the good work and most importantly enjoy this time with your son. Mine is 12 now, he'll be 13 soon, it went by WAY too fast.