Confidence, Too Confident - My Dilemma

I admit to being a novice in the world of popup camping.  I've done it 3 times -  last Fall up north, April in Georgia and May, I went to Maumee State Park in Ohio.  Since that Maumee trip, the trailer sat, closed up, in our backyard.  Each of my three trips helped me gain confidence - pulling the trailer, setting it up, taking down, etc.  On each trip, I had a few problems but by the time I returned from Maumee, I felt good about my experiences and the knowledge I'd gained. We'll, from then till now, I didn't do anything with it, it sat closed up in the backyard.  So, a few weeks ago, I  set it up and that went pretty good. I decided  to take it down last week and as I was doing it,  I was proud of myself,  it was going so great - confidence that's what I had, great confidence - apparently, too much confidence because, I forgot to take off the safety arms and what a mess.  There are two and they fit on a front and back strut so if there's a malfunction, the roof can't collapse. By not taking them off,  I jammed them and couldn't get the roof up or down. Thankfully, Larry was here and working together we fixed the problem and it doesn't look like damage was done - whew! So today, I decided to hitch the trailer to my Explorer - yep, really confident that I could do it - started turning crank to lift front end of trailer and, it stopped - I couldn't get it to go up for coupler to be higher than ball.  I looked at the bottom of the trailer and the front stabilizers were in the air - crap, I forgot to put the four stabilizers up.  I corrected the problem and looks like no damage to rear stabilizers - whew! There's a fine line between the confidence that I need to go on trips with the trailer and too much confidence where I create real problems for myself and potentially can damage the trailer.  I'm working to blend the "confidence" and "too much confidence" and then, maybe, be "cautiously confident". Also, I need to remember the whole, "you gotta have a plan man" and am making lists so that every time I do something with the trailer, I'll use these lists as reminders and hopefully stop having these kind of issues. I can get frustrated and sometimes want to kick myself for stupid mistakes but, in the end, I love being a "solo camping grandma" and just will keep going till I can't go no more.