I doubt this will be an issue as it wasn't one when Demon's Souls players transitioned into Dark Souls. A lot of the fun and difficulty comes from exploring areas and enemy attack patterns for the first time.
From Software has even shown that they are aware of what people expect and throw a wrench in their plans. Like how some players allowed themselves to be killed by the first boss, thinking it was pretty much a guaranteed death like in Demon's Souls (I know you can kill the tutorial boss in Demon's Souls.) Vinny even said some enemies in DS2 would counter back-attacks because it was so efficient before which will catch even seasoned players off-guard.
I'd love to go fully digital, however I'm concerned about harddisk space as well as pricing. The online store I usually buy from offers new games for very cheap, a lot of stuff in the PS store is quite a bit more expensive. My hope is they take enough lessons from Steam with daily or at least weekly sales.
Meh, Jeff not showing any respect to anything he doesn't understand or is interested in is nothing new. It shows when he couldn't do an upskirt shot, I'd have applauded the devs for not allowing it (although I wish there was a more elegant solution.) I remember in Valkyria Chronicles, you could look at the models, but the female ones you couldn't scroll below the belly.
The problem is that you're probably matched with a lot of smurfs who can't fathom the concept of completely new players. If you wanna avoid some of that, play a few botgames, tell people that you're new to the game and maybe have them give some advice, practice mechanics like last hitting, etc. to get accustomed to the game.