As a Captain I've flown with probably at least 100 different FOs over the last several years and only two of them bought hours via Gulfstream or a similiar program. Both of these guys were older/career changers. I would not recommend buying time like that if SkyWest is a goal cause it doesn't seem to open the door here. Additionally, they absolutely will not budge on any of the minimums.

Buying a CRJ type rating would be a serious waste of money. Even if you had Bill Gates money I'd still tell you not to do it.

As far as Jepps go, start using them now. Thats all we use, and during the interview you'll be asked multiple questions concerning all the different charts. I probably spent a good 10 minutes on the Jepps alone during my interview.

This is an excellant time in your career to get the basics down really good. Don't take any shortcuts, and try to learn as much as you can. We actually had a guy several years ago get fired during EMB upgrade training because he didn't know how to turn the lights on at an uncontrolled airport.