You can do it, but it is a real pain
To me, the cost of my slip is well worth it. I only live one block from our marina and it got old really fast stepping the mast and trailering the boat (2006 Hunter 25). The other thing that you will regret is the potential for damage putting it on and off the trailer. The high freeboard makes the boat a royal pain to trailer if you have a crosswind. While I love the mast raising system and can do it myself very easily, it can put a lot of wear and tear on the rigging if everything doesn't go right (and we all know how that happens). I pull mine with a 2 wheel drive, V8 powered Ford Explorer, which I assume weighs a bit more than your Tacoma. While the Explorer has plenty of power to pull the boat, stopping is another story. I will never pull this boat down the highway with anything less than an F250 or equivalent. At this point, I pull mine out once a year for hull cleaning. Otherwise, it is in the water. Obviously though, I am in Texas, and can leave the boat in the water ready to sail year round.