As I recently went through this, Ill share my thoughts.
If you're unsure this is for you, try rentals, demo paddles or getting some seat time at the bare minimum.
The kayak I got is heavy. Heavy as in 85-90lbs. I did get it through Rocktown Adventures. It was a new 2016 that I got last fall. It pays to shop. Realizing that was a challenge to car topping and pretty much everything else, I adapted.
I made a diy PVC cart to help with getting to and from the water. Haven't tested it as yet as just finished the paint on it.
I have some tall ceilings in my garage, so I went with a hoist setup. It's great. I pull into the garage with the kayak on the car, and up it goes. When I want to head out, I lower it, strap it down, and go.
There are number of solutions to aid with car topping. I've got a regular Yakima roof rack fro. Rackswarehouse.com. They ran a 20% off deal for a long while. There is an extension type bar that overhangs your car to the side while attaching to your rack. This allows you to put one end up and then work the other onto the rack. I think the part is RUSL from rhino racks.
On PFDs, I wanted a type ii. That's the type that will help in righting you face up in event you're unconscious. I am a fairly decent swimmer. If im going into the water, I want my head up and out. The problem is that most/all fishing geared PFDs are type iii. These aren't as likely to right the swimmer. So what to do... I found Cabelas makes a type ii inflatable. Bonus is that it's light and cooler than most. Negative is it's an inflatable. I've tested the bladder and will be doing the co2 shortly.
Paddles - People say spend your money here. I think that's an ideal world call. Yes, using $30 paddles from Wally World suck, but they work. That said, if you're on the water for a long time, then I recommend investing.
Hope it helps.