If you ever want to make the move, now is a pretty good time to give it a try. It's gonna take 5 or more years to break even, but over the next 35 years...you can do the math. g550 time is a nice thing to have in your back pocket when the airlines hit the next down turn.
If you live near a domicile with one of the majors...maybe focus your efforts on that one. Living in base is the best deal going at the airlines.
My dad was a career corporate guy, mainly with the same company. They sold the plane 3 years before he planned on retiring and went to a fractional to provide their lift. He always dissuaded me from going the corporate route. I never questioned it and went the airline route. Been furloughed twice and worked for 3 companies that are no longer in business.
Things are good now, though.