I think it might help to remember the investment strategy VC firms have. No matter how you structure a startup, it is more likely than not to fail; that's what companies do. The winners in an investment portfolio have to pay for the losers, which mean the winners have to pay big. And funds themselves have lifespans; for several reasons, they need to reach an answer on investments within a set timespan.
I think not raising money at all is a great strategy, and when it's viable, it's probably always superior. But if you're going to raise at all, slogging it out on pure sweat equity isn't a great way to build up credibility for an A-round. It might have been in 1999, but I don't think it is now; now, I think if you want to raise an A-round, the happy path is to raise a syndicated seed round first, and clearing the way for that seed round is probably one of the 3 biggest things you get out of YC.