Well I think we agree more than we disagree, honestly, even though it seems, at first glance, like there is a big gulf between our opinions.
Having an education and working hard improves your chances... That, I agree with. So if bootstraps just means "working hard to achieve your goals," then sure.
However, that is not how they tend to be used. The people who use the whole "pull yourself up by your own bootstraps" thing are making a more fatalistic (deterministic?) argument. They tend to argue against wealth redistribution, against social safety nets, against any sort of financial regulations, on the basis that people should "pull themselves up by their own bootstraps." Not saying this is you, but they also tend to disregard the fact that literally tens of millions of kids have done exactly the right thing, and still can't find a job, support themselves, buy a house, afford kids, etc. It is a real problem, and I think the bootstraps thing is used primarily as a means of disregarding the very real concerns people have.
Mathurin does it all the time. He is what I call a strict conservative: he believes inequity is totally natural, even desirable. When he talks about bootstraps, it isn't the reasonable position you have presented... it is an ideologically loaded statement that implicitly condemns a whole swath of people, irrespective of the facts.