There are a lot of products out there, but we found as starter kayakers it was very difficult to navigate what we do and do not need. Below is what has worked for us.
Eddyline touring kayaks
Touring kayaks are best for our planned open water, overnight adventures. For the Midwest, we didn't need much longer boats than 14 feet. We also needed a boat our 9 year old could grow in to without being overwhelmed at the start.
After a few years of paddling, I am in love with my Equinox. I find the weight is within my strength to portage loaded or unloaded. It is very stable and I do not get sea sick like I was worried I might in wavier conditions.
Tom, however, is not 100% pleased with the Denali. The extra storage has been a nice perk, but he feels very "tippy" and is unnerved in any rough water. His boat performs very well in rough waters, but the sensation of rocking and pitching if his center of balance gets off leaves him feeling unsure when I do not.
Ozzy's only complain about the Rio is that we paddle so much more efficiently than he does. When backpacking it is easy to gauge when he needs a break, but on the water, our arm strength is so much greater than his that he feels like we put too much pressure on him to keep up.
Yakima Rack-N-Roll Trailer
Our trailer has been the single best purchase of all our kayaking gear. While it was an unnerving expense at first, the ease and convenience has been worth every penny. We can load and go quickly without having to change out the truck in any way. We do not have to load on the car top which at our "advancing age" (lol) was a concern of mine. The boats also store in the garage on the trailer and we can pull it in and out to clean and dry the boats. It is so light weight that I can move it with one hand on my own. Many people have inquired about our trailer while we are out, so it must not be that common. For 3 boats, it is certainly the way to go.
This is the number one piece of gear to be comfortable in since you need to wear in 100% of the time. Definitely get a kayak specific life jacket meant for hours of paddling so that you have the range of motion you need. There are so many good options, really as long as you like the color and the pockets, you probably can't go wrong.
This has been the trickiest part of our kayaking start up. With the variety of weather conditions we plan on kayaking in, it has been hard to decide what we do and don't need right away, what we are safe but comfortable in, and what products are the best. We did get dry suits for Isle Royale, but only had 2 paddles where we felt it was worth wearing them- as we were very hot and restricted in them. When the weather was bad they did give us a great feeling of security and safety, but 99% of the time we preferred to paddle out of them. I would recommend a light cover up paddle jacket, rain pants, good warm neoprene gloves, neoprene socks, and paddle boots or sandals that strap over the thick socks. As long as you have a waterproof outer and are dressed for movement, dress as you would for backpacking underneath. Pack a dry bag of emergency clothes just in case, but you don't have to have fancy paddle clothing to get started.