It is possible the OpenSSH funding, since it is done through the OpenBSD Foundation, could, at the Foundation's discretion, go toward LibreSSL, since it's the same group.
No it's not. Libressl is a different team; one that feels a fork was more appropriate than just fixing the problems in openssl. IMHO, libressl is a mistake. It's splitting resources over something that needs to be as air-tight as possible. I'd much rather have 1 really really good ssl library that everyone uses instead of 2 so-so ones.
That's reasonable, but those aren't the options at play here. Not only because GnuTLS is already a thing, but the chances of OpenSSL becoming really really good are questionable.
An OpenBSD guy gave a talk a few weeks back where he said that Heartbleed wasn't the reason for the split, it was the reason for digging into the code and realizing that OpenSSL under current leadership isn't capable of being a really really good option.