I've only spoken with a few people that worked at SoA (and this was a few years ago so maybe things are changing now), but the impression I got from them is that a lot of people there are out of touch with what people actually want. That, and the leadership is about as risk averse as they come.
It makes sense when you look at the games they decide to localize: Hyperdimension Neptunia is a straight-up cash grab at anime fans, so of course they'd localize it. Yakuza 5 on the other hand is a slightly harder sell, especially since they can justify any attempt at localizing the game with "poor sales" of the previous games.
We're probably seeing that same kind of risk aversion here. Someone, somewhere has probably made the case that the classics only sell when they're bundled together and someone above that person probably listened. In the case of OutRun, they can always point to "poor sales" of the PS3/360 port of OutRun 2SP (nevermind that it was available on the marketplace for a little over a year).
As an aside, I asked all the people I spoke with how VF5:FS managed to get past the fun police. None of them could give me an explanation.
Sega took their time with the GG VC releases and the first batch of 3D classics, so I'm still hopeful for a US release. Last announcements came in a Nintendo direct, so I would expect that to be the case here. Knowing SEGA, they will probably wait until after the release of Sonic Boom to announce anything.