I don't know, the challenge from what I've played in Alpha will be coordinating things with friends, having the right people along rather than the ships. The game isn't just about ships after all, there's combat inside them, on planets, on stations and just floating about in space with guns, there's research, mining, engineering, medical, information running, racing.. and more. The ships people pledge for now might give them a kick start or reduce the initial play time before they can go into a profession like mining, but it wont' keep them ahead for long and it won't lessen the challenge of having to pilot a ship or make the most of it. Log into any alpha server and you'll see pilots struggling to land a ship they've owned for 6 months, not because the controls are hard (they really aren't) but because they've not spent enough time in that ship to get use to it. Amusingly with the next update there's a lot of changes coming that'll change it again.
As an Eve player I'd put it to you like this, imaging starting to play Eve now, you'd be behind wouldn't you? I'd argue you'd be MILES behind established players and why the hell not? They invested all that time after all? Star citizen needs funds to be finished, without these ships it wouldn't exist so isn't a pat on the back with ships that are going to be outdated from the day the game launches OK? Star Citizen doesn't have character leveling etc so the only thing to gear up on is gear, ships, knowledge and connections. Whilst you can currently grab ships, you can't really do the rest until the game is out and it comes out at the same time for all of us (or never if it falls on it's ****).
Essence of gaming for me is interactions, not challenge. If I'm having fun with friends I'm happy as larry, challenge is just an added bonus and seeing as I have a very good fighter and still can't take on a skilled pilot in a much cheaper ship - I see challenge frequently. Like I said, owning it doesn't make it work to it's full potential if the pilot is pants!
If in doubt hang off and look at it after release, nothing lost.