Mink

I'll second the Bombardier SSD. Excellent event, top-notch program, great speakers, and it's free (other than your own hotel / travel / meals).

You sound like you want to go about this in the correct fashion, and although I admittedly only skimmed through some of the above posts, it seems like you're getting good advice.

I flew the CJ3 and the CJ4 single pilot for the owner's family and friends, and I flew in the right seat for the owner once he got his type rating.

My single pilot operations were challenging at times - it's a lot to manage for one person, especially when things conspire against you (weather, passengers, etc.). I came from a single-pilot military background (had a crew, but was the only pilot) and I can say some of the CJ flying filled up my task bucket pretty quickly. On the other hand, it was a lot of fun and satisfying to "run the show" all by myself.

Being crewed with the owner was a different set of challenges. Good pilot, but piloting was not his profession. And although the differences between a dedicated, talented, and thorough pilot vs a "professional" pilot can sometimes be subtle, they are there. All that said, I highly recommend you find a "professional" pilot to assist you in getting your CJ familiarity and experience (or whatever light jet you end up with).

I also highly recommend, once the time comes, you do your type rating training with an established training provider IN A SIMULATOR. The owner I worked with got his initial type rating in the aircraft. Later on I insisted we do a recurrent together in a nearby sim facility. It was a wakeup call for the owner, as the sim exposed him to things he had not seen during his aircraft training. To his credit he stepped up to the plate and made it through just fine.

Good luck with your pursuits.