The Pampered upbringing doubles your starting money (1000) at the cost of willpower. 1000 really isn't that much.
As for a bigger ship, Victor Steele explicitly wants his heir to work their way up from something roughly approximating nothing (aside from the Nursery Deck, an entire Hangar for whatever ships you end up acquiring, food and fueling* costs), to ensure they have what it takes to run Steele Tech. It would also diminish the sense of progression when you get bigger, better ships, and also, it would have required the ship code to already be in