Get yourself a 98 chevy Silverado regular cab with a 350 for pulling your boat. Then get yourself an 01 honda civic coupe for daily driver.
Explanation: Old truck will pull the boat fine and is reliable and you can wrench it yourself. The civic will get great gas mileage and get you from point A to point B and will be easy to work on as well. The added benefit is when you go on a big trip with your buddies no one will want to ride in your reg cab or crunch up in a tiny civic. You pay for gas/food and drive their rig.
The benefits: you save 4000/year in depreciation. Another 2000-2500 in fuel. Insurance and registration will be a wash...2 liability only rigs vs 1 full coverage. Take that 6500/year and stick it in an IRA and retire a few years early or use it to cover tag applications and hunt costs plus a healthy gear budget