Basically, there are tell tale signs here and there if you read DVDs sites
as frequently as I do. It really depends on the studio.

I will try to break it down:

Starting from about 2 years ago, Fox usually tries to release the best edition the first time around (Moulin Rouge, Abyss, ID 4, Fight Club). The re-leases are usually bare bone or P&S Editions

Before the Ultimate Edition line was dropped, there is always a slim chance for Universal to re-lease older movies (The Mummy, Meet Joe Black, ets). Now, I buy Universal DVDs with confidence because the studio releases pretty good DVDs the first time around, and offering different editions, too.

Buying Dreamworks DVDs is very safe because it usually tries to release the best edition the first time around

WB usually does not re-release DVDs unless it is for aniversary purposes and big movies ( Singin' in the Rain SE, Harry Potter, etc). First time around, WB will release bare bone 1 disk editions except for blockbusters. The re-leased versions usually get 2 disk SE treatments and will come in Harry Potter pacakges( Amadeus SE, etc ).

Paramount did not start doing re-release until this year. When the studio does do that, it usually focus on certain series ( Star Trek, Jack Ryan Collection, etc ). If the first release is a 2 disk SE, it is unlikely to re-leased any time soon ( Forrest Gump ).

Buena Vista / Disney usually does not do re-leases, either. Since the introduction of Vista Series, BV tries to get some movies into VS the first time around ( Who Framed Roger Rabbit ). When Disney does re-leases, the newer edition usually will be the same with the old (A bug's Life ). So buying VS or Disney DVDs are pretty safe.

MGM usually does not do re-releases, even though the the first editions are usually bare bone, until recently ( Silence of the Lamb SE, Die Another Day SE ).

Columbia is the most likely to re-release DVDs; however, there are always news that Columbia will do re-releases when some DVDs are released for the first time ( Panic room, Resident Evil, Spiderman ). If a blockbuster movie ( XXX ) only gets a 1 disk treatment the first time around, it is almost a certainty that a SE or Superbit is on the way. This Studio is the most unpredictable.

Out of the DVDs I own, I have only had to buy a re-lease for about 5 movies. Of which, most of them are from Columbia.