I personally trailer mine. The lake near me is 20min and this allows me to fill it up from a gas station pump instead of a marina pump. Launching wise, if you have 2 experienced people, one that can back up a trailer and another that can properly handle and maneuver your boat in the water and around the dock, its not an issue at all. For me, depending on who I'm with, it takes me a matter of minutes with the time really being just me, or someone else, backing up the trailer down the ramp. Getting it on and off the trailer is a piece of cake.
Like others have said, leaving the boat in the water has its risk with leaks and making sure your bilge pump works in the event you do. If you do go that route of a leaving it in a slip, definitely have a good mooring cover.
I never had the chance to really leave my boat at a slip, but I keep my boat in my garage as I enjoy having easy access to it do whatever I want. Loading the boat and preparing it for usage is convenient as I can easily put all my equipment, vests, tubs, skis, poles, cooler, or whatever I want, all in my garage at the house. At the end of the day, wash the boat, unload all my wet equipment and gear to dry out and when the next time comes to use it, just load it with whatever I need that day. If I'm just going out with friends to relax and fish, can leave the tubes and skis behind, and vice versa if I'm bringing kids out. I don't have to always have to have everything on the boat with items taking up space.
Additionally, with trailering, it gives me the opportunity to drain any accumulated water in the bilge and, by keeping the boat in the garage, it isn't exposed to the high humidity, heat, rain, or other weather conditions that may wear out my seats of create an environment for mold. Since I had my boat repaired at the dealership for almost a year straight, even with dropping off it off with a nice vented mooring cover to be used when it isn't worked on, I picked up my boat and found mildew on my seats and some wear due inherent to a boat sitting outside on the trailer for a year. As I try to keep everything clean and neat, it hurt a bit but glad I can keep it in a garage. And when it comes to maintenance, its VERY convenient to work on it on a trailer in my garage with overhead lights and access to all my tools. Plus I can get under the boat to check my intake grates and impellers.
Ultimately, its a personal preference. If it is only you taking it out or you don't have anyone else to help you with it, then wet slip may be ideal for you, unless you are comfortable with the time involved with putting bumpers on, tying up the boat to the dock and so on. I think it takes me the same time to do that that as it is for me to install and remove the mooring cover on my boat by myself. I had the opportunity to store a boat in my garage, which I preferred, and I picked my boat because it was the biggest boat I could get that would fit in there. For me, Id recommend keeping it stored indoors to ensure its safe from the elements, clean, and don't have to worry about worn because of the elements.