The Cheyenne 400 LS is a good looking bird. I'll admit I had to look it up.
My buddy decided to jump into aviation a little late in life. It has been interesting to watch his progress. He started off renting planes and about 10 hours in he knew this was a thing for him so he bought an old Money 20C and got his tickets in that plane when possible. I think he flew around 500 hours a year at one point. Luckily he had his own business to help support this. He then worked for a jump school to build time and get paid for it. This lead to a while working charter and then jumped into airline. The Covid period didn't allow him to fly much, but it allowed him a lot of home time with his young family. He is now going off for his captain rating with SkyWest. He still has his business, but it is no longer the primary as the airline gig finally pays the bills.
He likes to call and tell me about the stupid things that happen in charter/airline life and I always would respond with "hashtag Pilot Life". The life of the low hour pilot getting started and building time is not a great experience.
I will say that Skywest has worked out really well for him. He was able to secure SFO as his home base almost right away, so he would spend time at our house, and after maybe 2 months he was able to transfer over to his home airport. This eased the family life greatly. He has been there since. sadly his Mooney now collects dust in a hangar. He should probably sell it, but he is attached to it, and finally has it all upgraded with new interior and new paint, and modern avionics. They are good planes that don't drink the fuel too fast.
P.S. He has an architecture degree, worked that for a while and found it boring. He ended up falling back on one of his other passions, 4x4 adventures and started his business doing custom fabrication where he did many things but primarily competition rock crawlers and was crew chief for the Red Bull team. This changed more into a small manufacturer of jeep parts and this is what his business is today. Currently has a new Bronco on order as he would like to develop some parts for it. He rarely does just one thing, usually has his eye on several things and does them all pretty darn well. He is also in boats, powered and sail.
Sorry, that was sort of off topic, but sort of following a buddies career.