So is there any road to a Gulfstream job that doesn't include being onsite when a plane is purchased?
Most of the companies that require a type prior to being hired are usually not the ones to go to work for (i.e. 135 ops trying to make as much profit as possible or an individual that barely had the money to purchase the aircraft and can't afford to operate it correctly). By the same token, buying a type on your own dime is not looked upon favorably either. The really good companies hire the right "personality" that fits into their culture, and if not already typed will send them to initial. Usually this comes from either knowing someone personally that flies for the company or being recommended by someone that knows the CP or someone else in the flight department. A word of caution though, it's also not looked upon very favorably if you accept a job, get the type, and then jump ship for a better position or decide that the Gulfstream life is not for you. Aviation is a very small world and word gets around. Good luck, network as much as possible and be courteous to whomever you meet. You never know, the person sitting next to you at the bar/restaurant may be CP or CEO of a company operating an aircraft that you want to go to work for.