Those aren't silly questions at all.
It's fantastic that you have such a nice variety of stuff available to keep you motivated and interested in working out. Don't let any of it gather dust; play with it all!
I exercise almost every day (maybe three days off a month, on average), but I don't do the same exercise every day. I've read that lifting weights is best done every other day so that muscle fibers have a chance to repair and rebuild in between workouts; I stick to that. Walking is about the only thing I do daily; some days it's the only thing I do, other days it's combined with stationary biking or lifting.
Youtube is full
of videos about how to use particular equipment, how to design a workout program, how to maintain proper form while lifting, and so forth. It's an awesome resource for folks who don't want to or can't afford to go to a gym.
As for 30DS, I hear good things about it from some and "OMG, not for me!" from others. I say try it, but if it feels way over your head, don't beat yourself up about it. A lot of fitness videos are designed for people who are starting out fairly fit already, so if you've been somewhat sedentary, you may find some videos really tough to keep up with at first.
When I find something I can't yet do, I get frustrated for about half an hour, then set that thing as a goal. When I first got my stationary bike, I couldn't ride for more than five minutes (totally sedentary lifestyle plus thirty years of smoking that I recently quit meant absolutely NO stamina). I carped and moaned about not being able to do it, but a month later I was going for a full thirty minutes. That was my goal and I met it.