Coming into this late here, but I would say you might sit at $3/$6 with $300 and that would give you a good size stack. You seem to be saying that is your bankroll, and that (since it is one buyin) is not enough of a bankroll for $3/$6.....or $2/$4, or $1/$2.
I do agree that if you have other money that you can re-deposit if you bust out of that original $300 then you "bankroll" is not $300, it is unlimited (until the divorce, then its 1/2 of unlimited

).
If you are trying to run up a set amount through the levels, IMO, you have to leave yourself more than one buyin at a level to keep from busting out with the type of run you describe. By jumping up to $1/$2 too quickly you didn't leave yourself an out to fall back on.
You titled your thread "I knew it would happen" and I think that is right. You knew this would happen if you kept pushing up through the levels. At some point you hit a level that you can't beat OR just get a bad run of cards, and when that happens you need to have enough left to take one step back. You now have to either take 3-4 back (.10/.20) or redeposit.
Just my opinions, take em or not...
Good luck building it back up.