One of the 'road blocks' people face for riding bikes is the bike breaking. With youtube we can all look up things now on bike repair and I hope that more people use this outlet now because its easier than ever to repair your bike.
One alternative is to just buy a cheapo bike every year and it maybe possible to use parts off an old bike to help with repairs.
I bought a Pro Bike stand instead of the cheaper homeowner grade version. I've had no regrets when it comes to quality tools. I'm not saying that anyone should spend more than they feel comfortable. It's kind of a learning curve, so after they're committed, I would say to check yard sales and discount stores first. A little at a time as necessary. Rather than buying a screw driver set, a little bit kit and racheting driver saves money and works well.
I think that a starter kit for DIY repair can start out under $100. I like your recommendation. YouTube vids and a handy repair book is less than a bike shop mechanic. Then they'll learn how to fix a minor repair that could get them home.
Used bikes that have seen little use is another option.