With the shortage of pilots I'm sure you can just apply and get called right away. They'll hire direct entry captain non typed if you sign a training contract. Otherwise if you just want to see what it's all about fly right seat somewhere and they usually upgrade within months.

If you want the best quality of life, generally go for the bigger aircraft that have a flight attendant. Typically the bigger jets have less last minute fights, you know where you'll be flying at least a day or so before and flying is generally better. If you're coming from Pt121 with lots of experience then I would try to go for a Pt135 operation rather than Pt91. At least 135 has somewhat of a structured environment with SOPs and CRM.

Unless you're flying for an owner, you can use the Netjets pay scale on here to see how much you'll generally be making for each type.

Flying is perfect for retirees. But in general, unless your operator has set schedules, your mindset should be that they own you for those days on. You can fly anywhere and your schedule can be changed any time. You can not expect to have any sort of regular schedule. Still, it's very laid back, awesome flying and you don't fly much(depends on fleet). You're just hanging out at hotels getting paid usually. The challenging part is that you are on the road for long stretches, 7 to 15 days so you need an understanding spouse/kids.

Best of luck.