Going to the water can be a pain... but it's good advice if you are close.
But... you are in luck. The 14' boats aren't very heavy, and the center of gravity is just about at the rear seat back. AND... The best part of all.... there is a nice flat strip down the bottom !!!!!!
So.... if you have a pair of bottle jacks, floor jacks... or better yet... motorcycle jacks... you can simply lift it off the trailer, and do the work needed in the comfort of your driveway. If you use bottle, or floor jacks... put a hunk of wood under them so you don't gouge the hull. Also, if you use bottle jacks... make sure you have the slip on adapters so you aren't lifting with a single 1" post. (that won't be stable)
Needless to say... if you do it... you need to start level, and you need to keep drunk buddies away from it. (don't want it getting knocked over) But... the flat is about 8" wide... so it's really very stable.
I had to get the trailer out from under mine because the title was screwed up... and I had to take it in to be weighed.